As filed with the Securities and Exchange Commission on November 23, 2010.April 8, 2011

Registration No. 333-_____333-      

 

UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

 

Form S-4

REGISTRATION STATEMENT
UNDER THE SECURITIES ACT OF 1933

 

Berkshire Hills Bancorp, Inc.

(Exact name of registrant as specified in its charter)

Delaware		6036		34-3510455
(State or other jurisdiction of incorporation or organization)		(Primary Standard Industrial Classification Code Number)		(I.R.S. Employer Identification Number)

24 North Street Pittsfield, Massachusetts 01201 (413) 443-5601		Michael P. Daly President and Chief Executive Officer 24 North Street Pittsfield, Massachusetts 01201 (413) 443-5601
(Address, including zip code, and telephone number, including area code, of registrant’s principal executive offices)		(Name, address, including zip code, and telephone number, including area code, of agent for service)

 

Copies to:

Lawrence M. F. Spaccasi, Esq. Marc Levy, Esq. Luse Gorman Pomerenk & Schick, P.C. 5335 Wisconsin Avenue, N.W., Suite 780 Washington, D.C. 20015 (202) 274-2000 Facsimile: (202) 362-2902		Matthew DyckmanMichael Krebs, Esq. Rosemary SpazianiAdam Ghander, Esq. SNR Denton USNutter McClennen & Fish LLP 1301 K Street, N.W.Seaport West Washington, D.C. 20005155 Seaport Boulevard (202) 408-6400Boston, MA 02210 (617) 310-9000 Facsimile: (202) 408-6399(617) 310-9000

 

Approximate date of commencement of proposed sale to the public: As soon as practicable after the effective date of this Registration Statement and the conditions to the consummation of the merger described herein have been satisfied or waived.

If the securities being registered on this Form are being offered in connection with the formation of a holding company and there is compliance with General Instruction G, check the following box.o

If this Form is filed to register additional securities for an offering pursuant to Rule 462(b) under the Securities Act, check the following box and list the Securities Act registration statement number of the earlier effective registration statement for the same offering.o

If this Form is a post-effective amendment filed pursuant to Rule 462(d) under the Securities Act, check the following box and list the Securities Act registration statement number of the earlier effective registration statement for the same offering.o

Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, or a smaller reporting company. See the definitions of “large accelerated filer,” “accelerated filer” and “smaller reporting company” in Rule 12b-2 of the Exchange Act. (Check one):

Large accelerated filero		Accelerated filerx		Non-accelerated filero		Smaller reporting companyo

If applicable, place an X in the box to designate the appropriate rule provision relied upon in conducting this transaction:

Exchange Act Rule 13e-4(i) (Cross-Border Issuer Tender Offer)

o

Exchange Act Rule 14d-1(d) (Cross-Border Third-Party Tender Offer)

o

Exchange Act Rule 13e-4(i) (Cross-Border Issuer Tender Offer)o

Exchange Act Rule 14d-1(d) (Cross-Border Third-Party Tender Offer)o

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CALCULATION OF REGISTRATION FEE

Title of each class of securities to be registered		Amount to be registered				Proposed maximum offering price per share				Proposed maximum aggregate offering price				Amount of registration fee				Amount to be registered				Proposed maximum offering price per share				Proposed maximum aggregate offering price				Amount of registration fee
Common Stock, $0.01 par value per share			2,684,317 shares	(1)		$	10.965	(2)		$	29,433,536	(2)		$	2,099	(3)			6,203,000 shares	(1)		$	13.115	(2)		$	81,352,345	(2)		$	9,445	(3)

 

The registrant hereby amends this registration statement on such date or dates as may be necessary to delay its effective date until the registrant shall file a further amendment which specifically states that this registration statement shall thereafter become effective in accordance with Section 8(a) of the Securities Act of 1933, as amended, or until the registration statement shall become effective on such date as the Commission, acting pursuant to said Section 8(a), may determine.

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PRELIMINARY JOINT PROXY STATEMENT/PROSPECTUS
DATED APRIL 8, 2011, SUBJECT TO COMPLETION

PRELIMINARY PROXY STATEMENT/PROSPECTUS		DATED NOVEMBER 23, 2010, SUBJECT TO COMPLETION

[BERKSHIRE HILLS BANCORP, INC. LOGO      ROME BANCORP, INC. LOGO

MERGER PROPOSED — YOUR VOTE IS VERY IMPORTANTLOGO]

The boards of directors ofDear Berkshire Hills Bancorp Stockholder:

On December 21, 2010, Berkshire Hills Bancorp, Inc. and Romeentered into a merger agreement to acquire Legacy Bancorp, Inc. have agreed toin a merger of our companies.stock and cash transaction. If the merger agreement is approved and the merger is subsequently completed, each shareLegacy Bancorp, Inc. will merge into Berkshire Hills Bancorp.

The shares of RomeLegacy Bancorp, Inc. common stock owned by each Legacy Bancorp, Inc. stockholder will be converted into the right to receive either 0.56580.56385 shares of Berkshire Hills Bancorp, Inc. common stock or $11.25and $1.30 in cash, subject to 70% of Rome Bancorp, Inc. common stock being exchanged forcash. If Berkshire Hills Bancorp, Inc.’s common stock and 30% of Rome Bancorp, Inc. common stock being exchanged for cash.Legacy must divest deposit liabilities in order to comply with a requirement contained in any regulatory approval, and if the weighted average deposit premium that Berkshire Hills Bancorp, Inc.’sreceives for those divested deposits exceeds 350 basis points, then Berkshire Hills will be required under the Merger Agreement to make an additional cash payment to Legacy stockholders that, in the aggregate, will continueequal 50% of the premium in excess of 350 basis points (net of applicable taxes on such excess premium). Such payment would occur following completion of any such divestiture which is anticipated to own their existing shares. Afteroccur after completion of the merger, we expect that current Berkshire Hills Bancorp, Inc. stockholders will own approximately __%Merger.

The maximum number of the combined company and Rome Bancorp, Inc. stockholders will own approximately __% of the combined company. Berkshire Hills Bancorp, Inc. common stock is listed on the Nasdaq Global Select Market under the symbol “BHLB.” On _______, 2010, the closing priceshares of Berkshire Hills Bancorp, Inc. common stock was $_____.estimated to be issuable upon completion of the merger is 6,203,000.

As a result of the merger, Legacy Bancorp, Inc. stockholders will become stockholders of Berkshire Hills Bancorp, Inc. is offering approximately _______ shares

Your board of its common stock to Rome Bancorp, Inc. stockholders.

We expectdirectors has unanimously determined that the merger to generally be tax-free for federal income tax purposes solely to holdersand the merger agreement are fair and in the best interests of Rome Bancorp, Inc. common stock to the extent they receive Berkshire Hills Bancorp, Inc. and its stockholders and unanimously recommends that you vote “FOR” adoption of the merger agreement.The merger cannot be completed unless a majority of the issued and outstanding shares of common stock. Any cash consideration received will be taxable to Romestock of Berkshire Hills Bancorp, Inc. stockholders.

We cannot completevote to adopt the merger unless we obtain the necessary government approvals and unless the stockholders of Rome Bancorp, Inc. approve the merger agreement. Rome Bancorp, Inc. is asking its stockholders to consider and vote on this merger proposal at its special meeting of stockholders. Whether or not you plan to attend the Rome Bancorp, Inc. stockholderspecial meeting of stockholders, please take the time to vote by completing and mailing the enclosed proxy card to Rome Bancorp, Inc. and mailing it in the enclosed envelope.If you sign, date and mail your proxy card without indicating how you want to vote, your proxy will be counted as a vote“FOR” the merger and the transactions contemplated by “FOR” adoption of the merger agreement. If you do not return your proxy card,fail to vote, or if you do not instruct your broker how to vote any shares held for you in “street name,” it will have the same effect as voting “AGAINST” the merger agreement.

In addition, Berkshire Hills stockholders will consider an amendment to our Certificate of Incorporation to increase the number of shares of common stock we are authorized to issue from 26 million shares to 50 million shares. This proposal is separate and distinct from, and not conditioned upon, the outcome of the stockholder vote for the proposed merger with Legacy Bancorp, Inc.

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The accompanying document is also being delivered to Legacy Bancorp, Inc. stockholders as Berkshire Hills Bancorp, Inc.’s prospectus for its offering of Berkshire Hills Bancorp, Inc. common stock in connection with the merger, and as a proxy statement for the solicitation of proxies from Legacy Bancorp, Inc. stockholders to vote for the adoption of the merger agreement and approval of the merger.

This Joint Proxy Statement/Prospectus provides you with detailed information about the proposed merger. It also contains or references information about Berkshire Hills Bancorp, Inc. and Legacy Bancorp, Inc. and related matters. You are encouraged to read this document carefully.In particular, you should read the “Risk Factors” section beginning on page 7 for a discussion of the risks you should consider in evaluating the proposed merger and how it will affect you.

Voting procedures are described in this Joint Proxy Statement/Prospectus. Your vote is important, so I urge you to cast it promptly. Berkshire Hills Bancorp, Inc.’s management enthusiastically supports the acquisition of Legacy Bancorp, Inc., and joins with our board of directors in recommending that you vote “FOR” adoption of the merger agreement. We also recommend that you vote “FOR” the amendment of our Certificate of Incorporation.

Sincerely,


Michael P. Daly
President and Chief Executive Officer

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[LEGACY BANCORP, INC. LOGO]

Dear Legacy Bancorp Stockholder:

On December 21, 2010, Berkshire Hills Bancorp, Inc. entered into a merger agreement to acquire Legacy Bancorp, Inc. in a stock and cash transaction. If the merger agreement is approved and the merger is subsequently completed, Legacy Bancorp, Inc. will merge into Berkshire Hills Bancorp, Inc.

Each share of Legacy Bancorp, Inc. common stock owned by each Legacy Bancorp, Inc. stockholder will be converted into the right to receive 0.56385 shares of Berkshire Hills Bancorp, Inc. common stock and $1.30 in cash. If Berkshire Hills and Legacy must divest deposit liabilities in order to comply with a vote againstrequirement contained in any regulatory approval, and if the weighted average deposit premium that Berkshire Hills receives for those divested deposits exceeds 350 basis points, then Berkshire Hills will be required under the Merger Agreement to make an additional cash payment to Legacy stockholders that, in the aggregate, will equal 50% of the premium in excess of 350 basis points (net of applicable taxes on such excess premium). Such payment would occur following completion of any such divestiture which is anticipated to occur after completion of the merger.

The maximum number of shares of Berkshire Hills Bancorp, Inc. common stock estimated to be issuable upon completion of the merger agreement.is.

RomeAs a result of the merger, Legacy Bancorp, Inc.’s stockholders will become stockholders of Berkshire Hills Bancorp, Inc.

Your board of directors has unanimously determined that the merger is advisable,and the merger agreement are fair to, and in the best interests of RomeLegacy Bancorp, Inc. and its stockholders and unanimously recommends that you vote FOR“FOR” adoption of the merger agreement.The merger cannot be completed unless a majority of the issued and outstanding shares of common stock of Legacy Bancorp, Inc. entitled to be cast vote to adopt the merger agreement. Whether or not you plan to attend the special meeting of stockholders, please take the time to vote by completing the enclosed proxy card and mailing it in the enclosed envelope.If you sign, date and mail your proxy card without indicating how you want to vote, your proxy will be counted as a vote “FOR” adoption of the merger agreement. If you fail to vote, or you do not instruct your broker how to vote any shares held for you in “street name,” it will have the same effect as voting “AGAINST” the merger agreement.

The accompanying document is being delivered to Legacy Bancorp, Inc. stockholders as Berkshire Hills Bancorp, Inc.’s prospectus for its offering of Berkshire Hills Bancorp, Inc. common stock in connection with the merger, and as a proxy statement for the solicitation of proxies from Legacy Bancorp, Inc. stockholders to vote for the adoption of the merger agreement and approval of the merger agreement.merger.

The place, dateLegacy Bancorp, Inc. stockholders have dissenters’ rights and timemay receive payment in cash of the Romefair value of their shares, excluding any appreciation in value that results from the merger. To maintain dissenters’ rights, a stockholder must (1) deliver written notice of its intent to demand payment for its shares to Legacy Bancorp, Inc. stockholders’before the special meeting of Legacy stockholders or at the special meeting but before the vote is taken and (2) either vote against the merger or not submit a proxy. See“Questions and Answers About the Merger and the Special Meetings” on page ii and“Rights of Dissenting Stockholders” on page 34. A copy of the section of the Delaware General Corporation Law pertaining to dissenters’ rights is included as follows:

The Rome Savings Bank
100 W. Dominick Street
Rome, New York
[Date]
5:30 p.m., local timeAppendix D to the accompanying Joint Proxy Statement/Prospectus.

This documentJoint Proxy Statement/Prospectus provides you with detailed information about the proposed merger. It also contains a more complete description of the Rome Bancorp, Inc. stockholders’ meeting and the terms of the merger. We urge you to review this entire document carefully. You may also obtainor references information about Berkshire Hills Bancorp, Inc. from documentsand Legacy Bancorp, Inc. and related matters. You are encouraged to read this document carefully.In particular, you should read the “Risk Factors” section beginning on page 7 for a discussion of the risks you should consider in evaluating the proposed merger and how it has filedwill affect you.

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Voting procedures are described in this Joint Proxy Statement/Prospectus. Your vote is important, so I urge you to cast it promptly. Legacy Bancorp, Inc.’s management enthusiastically supports the merger with Berkshire Hills Bancorp, Inc., and joins with our board of directors in recommending that you vote “FOR” adoption of the Securities and Exchange Commission.merger agreement.

Michael P. Daly		Charles M. SprockSincerely,
President and		J. Williar Dunlaevy Chief Executive Officer		President and Chief Executive Officer
Berkshire Hills Bancorp, Inc.		Rome Bancorp, Inc.Chairman of the Board

Joint Proxy Statement/Prospectus dated _______
and first mailed to stockholders on or about _________

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WHERE YOU CAN FIND MORE INFORMATION

Both Berkshire Hills Bancorp, Inc. and Legacy Bancorp, Inc. file annual, quarterly and special reports, proxy statements and other business and financial information about Berkshire Hills Bancorp, Inc. from documents filed with the Securities and Exchange Commission that have not been included in or delivered with this document.(the “SEC”). You may read and copy these documentsany materials that either Berkshire Hills Bancorp, Inc. or Legacy Bancorp, Inc. files with the SEC at the Securities and Exchange Commission’s public reference facilities.SEC’s Public Reference Room at 100 F Street, N.E., Room 1580, Washington, D.C. 20549, at prescribed rates. Please call the SEC at 1-800-SEC-0330(800) SEC-0330 ((800) 732-0330) for further information on the public reference room. In addition, Berkshire Hills Bancorp, Inc. and Legacy Bancorp, Inc. file reports and other business and financial information with the SEC electronically, and the SEC maintains a website located athttp://www.sec.gov containing this information. You will also be able to obtain these documents, free of charge, from Berkshire Hills Bancorp, Inc. atwww.berkshirebank.com under the “Investor Relations” link and then under the heading “SEC filings” or from Legacy Bancorp, Inc. by accessing Legacy Bancorp, Inc.’s website atwww.legacybanks.com under the “Investors” link and then under the heading “SEC Filings.”

Berkshire Hills Bancorp, Inc. has filed a registration statement on Form S-4 to register with the SEC up to 6,203,000 shares of Berkshire Hills Bancorp, Inc. common stock. This Joint Proxy Statement/Prospectus is a part of that registration statement. As permitted by SEC rules, this Joint Proxy Statement/Prospectus does not contain all of the information included in the registration statement or in the exhibits or schedules to the registration statement. You may read and copy the registration statement, including any amendments, schedules and exhibits at the addresses set forth below. Statements contained in this document as to the contents of any contract or other documents referred to in this Joint Proxy Statement/Prospectus are not necessarily complete. In each case, you should refer to the copy of the applicable contract or other document filed as an exhibit to the registration statement. This Joint Proxy Statement/Prospectus incorporates by reference documents that Berkshire Hills Bancorp, Inc. and Legacy Bancorp, Inc. have previously filed with the SEC. They contain important information about the companies and their financial condition. See“Where You Can Find More Information” on page 96. These documents are available without charge to you upon written or oral request to the applicable company’s principal executive offices. The respective addresses and telephone numbers of such principal executive offices are listed below:

Berkshire Hills Bancorp, Inc. 24 North Street Pittsfield, Massachusetts 01201 Attention: Investor Relations Department (413) 236-3239		Legacy Bancorp, Inc. 99 North Street Pittsfield, Massachusetts 01201 Attention: Investor Relations (413) 445-3513

To obtain timely delivery of these facilities. documents, you must request the information no later than ____________ in order to receive them before Berkshire Hills Bancorp, Inc.’s special meeting of stockholders and no later than ____________ in order to receive them before Legacy Bancorp, Inc.’s special meeting of stockholders.

Berkshire Hills Bancorp, Inc. common stock is traded on the NASDAQ Global Select Market under the symbol “BHLB,” and Legacy Bancorp, Inc. common stock is traded on the NASDAQ Global Market under the symbol “LEGC.”

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BERKSHIRE HILLS BANCORP, INC.

24 NORTH STREET
PITTSFIELD, MASSACHUSETTS 02101

NOTICE OF THE SPECIAL MEETING OF STOCKHOLDERS
TO BE HELD ON ____________, 2011

NOTICE IS HEREBY GIVEN that a special meeting of the stockholders of Berkshire Hills Bancorp, Inc. will be held at ___________________________, at __:00 _.m., Eastern Standard Time, on _______________, 2011, for the following purposes:

1. To consider and vote upon a proposal to adopt the Agreement and Plan of Merger, dated as of December 21, 2010, by and between Berkshire Hills Bancorp, Inc. and Legacy Bancorp, Inc., and thereby to approve the transactions contemplated by the merger agreement, including the merger of Legacy Bancorp, Inc. with and into Berkshire Hills Bancorp, Inc.;

2. The amendment of our Certificate of Incorporation to increase the number of shares of common stock we are authorized to issue from 26 million to 50 million;

3. To approve one or more adjournments of the special meeting, if necessary or appropriate, including adjournments to permit further solicitation of proxies in favor of the merger; and

4. To transact any other business which may properly come before the special meeting or any adjournment or postponement thereof.

The proposed merger is described in more detail in this Joint Proxy Statement/Prospectus, which you should read carefully in its entirety before you vote. A copy of the merger agreement is attached as Appendix A to this Joint Proxy Statement/Prospectus. Only Berkshire Hills Bancorp, Inc. stockholders of record as of the close of business on ______________, 2011, are entitled to notice of and to vote at the special meeting of stockholders or any adjournments of the special meeting.

To ensure your representation at the special meeting of stockholders, please follow the voting procedures described in the accompanying Joint Proxy Statement/Prospectus and on the enclosed proxy card.This will not prevent you from voting in person, but it will help to secure a quorum and avoid added solicitation costs. Your proxy may be revoked at any time before it is voted.

BERKSHIRE HILLS BANCORP, INC.’S BOARD OF DIRECTORS UNANIMOUSLY RECOMMENDS THAT YOU VOTE “FOR” ADOPTION OF THE MERGER AGREEMENT, “FOR” THE AMENDMENT TO OUR CERTIFICATE OF INCORPORATION, AND “FOR” THE ADJOURNMENT PROPOSAL DESCRIBED ABOVE.

BY ORDER OF THE BOARD OF DIRECTORS


Wm. Gordon Prescott
Corporate Secretary and General Counsel

Pittsfield, Massachusetts
_____________, 2011

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YOUR VOTE IS IMPORTANT!

WHETHER OR NOT YOU EXPECT TO ATTEND THE BERKSHIRE HILLS BANCORP SPECIAL MEETING IN PERSON, BERKSHIRE HILLS BANCORP URGES YOU TO SUBMIT YOUR PROXY AS PROMPTLY AS POSSIBLE BY COMPLETING, SIGNING AND RETURNING THE PROXY CARD OR VOTING INSTRUCTION CARD AND RETURNING IT IN THE POSTAGE-PAID ENVELOPE PROVIDED.If your shares are held in the name of a bank, broker or other nominee, please follow the instructions on the voting instruction card furnished to you by such record holder.

If you have any questions concerning the merger or other matters to be considered at the Berkshire Hills Bancorp, Inc. special meeting, would like additional copies of this Joint Proxy Statement/Prospectus or need help voting your shares, please contact Berkshire Hills Bancorp, Inc.’s proxy solicitor:

Phoenix Advisory Partners, LLC
110 Wall Street, 27^th Floor
New York, New York 10005
1-800-________ (toll free)
1-212-__________ (call collect)

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LEGACY BANCORP, INC.

99 NORTH STREET
PITTSFIELD, MASSACHUSETTS 01201

NOTICE OF THE SPECIAL MEETING OF STOCKHOLDERS
TO BE HELD ON ______________________, 2011

NOTICE IS HEREBY GIVEN that a special meeting of the stockholders of Legacy Bancorp, Inc. will be held at the ______________________________ at __:00 _.m., Eastern Standard Time, on _______________, 2011, for the following purposes:

1. To consider and vote upon a proposal to adopt the Agreement and Plan of Merger, dated as of December 21, 2010, by and between Berkshire Hills Bancorp, Inc. and Legacy Bancorp, Inc., and thereby to approve the transactions contemplated by the merger agreement, including the merger of Legacy Bancorp, Inc. with and into Berkshire Hills Bancorp, Inc.;

2. To approve one or more adjournments of the special meeting, if necessary or appropriate, including adjournments to permit further solicitation of proxies in favor of the merger; and

3. To transact any other business which may properly come before the special meeting or any adjournment or postponement thereof.

The proposed merger is described in more detail in this Joint Proxy Statement/Prospectus, which you should read carefully in its entirety before voting. A copy of the merger agreement is attached as Appendix A to this Joint Proxy Statement/Prospectus. Only Legacy Bancorp, Inc. stockholders of record as of the close of business on _________________, 2011, are entitled to notice of and to vote at the special meeting of stockholders or any adjournments of the special meeting.

To ensure your representation at the special meeting of stockholders, please follow the voting procedures described in the accompanying Joint Proxy Statement/Prospectus and on the enclosed proxy card.This will not prevent you from voting in person, but it will help to secure a quorum and avoid added solicitation costs. Your proxy may be revoked at any time before it is voted.

BY ORDER OF THE BOARD OF DIRECTORS


Kimberly A. Mathews
Corporate Secretary and General Counsel

Pittsfield, Massachusetts
_________________, 2011

LEGACY BANCORP, INC.’S BOARD OF DIRECTORS UNANIMOUSLY RECOMMENDS THAT YOU VOTE “FOR” ADOPTION OF THE MERGER AGREEMENT AND “FOR” THE ADJOURNMENT PROPOSAL DESCRIBED ABOVE.

DO NOT SEND STOCK CERTIFICATES WITH THE PROXY CARD. YOU WILL RECEIVE A LETTER OF TRANSMITTAL WITH INSTRUCTIONS FOR DELIVERING YOUR STOCK CERTIFICATES UNDER SEPARATE COVER.

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YOUR VOTE IS IMPORTANT!

WHETHER OR NOT YOU EXPECT TO ATTEND THE LEGACY BANCORP, INC. SPECIAL MEETING IN PERSON, LEGACY BANCORP, INC. URGES YOU TO SUBMIT YOUR PROXY AS PROMPTLY AS POSSIBLE BY COMPLETING, SIGNING AND DATING THE ENCLOSED PROXY CARD AND RETURNING IT IN THE POSTAGE-PAID ENVELOPE PROVIDED.If your shares are held in the name of a bank, broker or other nominee, please follow the instructions on the voting instruction card furnished to you by such record holder.

If you have any questions concerning the merger or other matters to be considered at the Legacy Bancorp, Inc. special meeting, would like additional copies of this Joint Proxy Statement/Prospectus or need help voting your shares, please contact Legacy Bancorp, Inc.’s proxy solicitor:

Phoenix Advisory Partners, LLC
110 Wall Street, 27^th Floor
New York, New York 10005
1-800-________ (toll free)
1-212-__________ (call collect)

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QUESTIONS AND ANSWERS ABOUT THE MERGER AND THE SPECIAL MEETINGS

The following are answers to certain questions that you may have regarding the merger and the special meetings. We urge you to read carefully the remainder of this Joint Proxy Statement/Prospectus because the information in this section may not provide all the information that might be important to you in determining how to vote. Additional important information is also availablecontained in the appendices to, and the documents incorporated by reference in, this Joint Proxy Statement/Prospectus.

If Berkshire Hills and Legacy must divest deposit liabilities in order to comply with a requirement contained in any regulatory approval, and if the weighted average deposit premium that Berkshire Hills receives for those divested deposits exceeds 350 basis points, then Berkshire Hills will be required under the Merger Agreement to make an additional cash payment to Legacy stockholders that, in the aggregate, will equal 50% of the premium in excess of 350 basis points (net of applicable taxes on such excess premium). Such payment would occur following completion of any such divestiture which is anticipated to occur after completion of the Merger.

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Under Delaware law, the Merger cannot be completed unless Berkshire Hills stockholders vote to adopt the Merger Agreement and approve the Merger. By this Joint Proxy Statement/Prospectus, Berkshire Hills’s board of directors is soliciting proxies of Berkshire Hills stockholders to provide this approval at the Internet sitespecial meeting of Berkshire Hills stockholders discussed below.

Under Delaware law, the SEC maintainsMerger cannot be completed unless Legacy stockholders vote to adopt the Merger Agreement and approve the Merger. By this Joint Proxy Statement/Prospectus, Legacy’s board of directors is soliciting proxies of Legacy stockholders to provide this approval at the special meeting of Legacy stockholders discussed below.

For a more detailed discussion of the material United States federal income tax consequences of the transaction, including the tax consequences of the aggregate divestiture premium (described on pages 68 and 70) that may be paid to Legacy stockholders as additional cash consideration for such stockholders’ shares of Legacy common stock, please see the section “http://www.sec.gov.Description of the Merger — Material Tax Consequences of the Merger” beginning on page 68.

The consequences of the Merger to any particular stockholder will depend on that stockholder’s particular facts and circumstances. Accordingly, you are urged to consult your tax advisor to determine your tax consequences from the Merger.

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Under the Delaware General Corporation Law, record holders of Legacy common stock who do not vote in favor of the proposal to adopt the Merger Agreement and who deliver a notice of intent to demand payment will be entitled to seek appraisal rights in connection with the Merger, and if the Merger is completed, obtain payment in cash equal to the fair value of their shares of Legacy common stock as determined by the Court of Chancery of the State of Delaware, instead of the Merger consideration. To exercise their appraisal rights, Legacy stockholders must strictly follow the procedures prescribed by Delaware law. These procedures are summarized in this Joint Proxy Statement/Prospectus. In addition, the text of the applicable provisions of Delaware law is included as Appendix D to this document. Failure to strictly comply with these provisions will result in the loss of appraisal rights. For a more complete description of appraisal rights, please refer to the section entitled “Appraisal Rights” beginning on page D-1.

Legacy stockholders also are being asked to approve one or more adjournments of the special meeting, if necessary or appropriate, including adjournments to permit further solicitation of proxies in favor of the Legacy Merger Agreement proposal, which we refer to as the “Legacy adjournment proposal.”

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Legacy’s board of directors also unanimously recommends that Legacy stockholders vote “FOR” the Legacy adjournment proposal.

Approval of the Legacy adjournment proposal will require the affirmative vote of a majority of the voting power of the shares of Legacy common stock present in person or represented by proxy at the special meeting and entitled to vote on the Legacy adjournment proposal. Abstentions will have the same effect as shares voted against the Legacy adjournment proposal, and broker non-votes will not affect whether the Legacy adjournment proposal is approved.

As of the record date for the special meeting, directors and executive officers of Legacy, together with their affiliates, had sole or shared voting power over approximately ____% of the Legacy common stock outstanding and entitled to vote at the special meeting.

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If you have instructed a broker to vote your shares, you must follow your broker’s directions to change your vote.

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Berkshire Hills stockholders also are being asked to approve an amendment to Berkshire Hills Bancorp, Inc. Certificate of Incorporation to increase the number of shares of common stock we are authorized to issue from 26 million to 50 million and to approve one or more adjournments of the special meeting, if necessary or appropriate, including adjournments to permit further solicitation of proxies in favor of the Berkshire Hills Bancorp Merger Agreement proposal or the amendment to the Berkshire Hills Bancorp, Inc. Certificate of Incorporation, which we refer to as the “Berkshire Hills Bancorp adjournment proposal.”

Berkshire Hills Bancorp’s board of directors also unanimously recommends that Berkshire Hills stockholders vote “FOR” the amendment to the Berkshire Hills Bancorp, Inc. Certificate of Incorporation and “FOR” the Berkshire Hills Bancorp adjournment proposal.

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As of the record date for the special meeting, directors and executive officers of Berkshire Hills, together with their affiliates, had sole or shared voting power over approximately ____% of the Berkshire Hills common stock outstanding and entitled to vote at the special meeting.

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If you have instructed a broker to vote your shares, you must follow your broker’s directions to change your vote.

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SUMMARY

This summary highlights selected information in this Joint Proxy Statement/Prospectus and may not contain all of the information important to you. To understand the Merger more fully, you should read this entire document carefully, including the documents attached to this Joint Proxy Statement/Prospectus.

The Companies

Berkshire Hills Bancorp, Inc.
24 North Street
Pittsfield, Massachusetts 01201
(413) 443-5601

Berkshire Hills, a Delaware corporation, is a savings and loan holding company headquartered in Pittsfield, Massachusetts that was incorporated and commenced operations in 2000. Berkshire Hills’ common stock is listed on The NASDAQ Global Select Market under the symbol “BHLB.” Berkshire Hills conducts its operations primarily through Berkshire Bank, a Massachusetts chartered savings bank with 48 full-service branch offices in western Massachusetts, northeastern and central New York and southern Vermont. Berkshire Bank’s experienced banking team offers comprehensive deposit, lending and wealth management products to personal and business accounts. Berkshire Hills is also the holding company for Berkshire Insurance Group, a full service Massachusetts insurance agency providing both personal and business insurance services. At December 31, 2010, Berkshire Hills had total assets of $2.9 billion, total deposits of $2.2 billion and total stockholders’ equity of $388 million.

On April 1, 2011, Berkshire Hills completed its acquisition of Rome Bancorp, Inc. (“Rome”) and The Rome Savings Bank. The aggregate merger consideration paid to the Rome stockholders was approximately 2,597,000 shares of Berkshire Hills common stock and approximately $22.1 million cash. At December 31, 2010, Rome had total assets of $327.2 million, total deposits of $225.3 million, total stockholders’ equity of $60.7 million provided through five full-service community banking offices in Rome, Lee and New Hartford, New York, all of which opened as branches of Berkshire Bank on April 1, 2011.

Legacy Bancorp, Inc.
99 North Street
Pittsfield, Massachusetts 01201
(413) 443-4421

Legacy, a Delaware corporation, is a one-bank holding company headquartered in Pittsfield, Massachusetts that was incorporated and commenced operations in 2005. Legacy’s common stock is quoted on the NASDAQ Global Market under the symbol “LEGC.” Legacy conducts its operations primarily through Legacy Banks, a Massachusetts-chartered stock savings bank offering products and services to individuals, families and business through 19 branch offices in western Massachusetts and eastern New York State. Predecessors to Legacy Banks have been serving the area’s financial needs since 1835. Legacy Banks’ business consists primarily of making loans to its customers, including residential mortgages, commercial real estate loans, commercial loans and consumer loans, and investing in a variety of investment and mortgage-backed securities. Legacy Banks funds these lending and investment activities with deposits from the general public, funds generated from operations and select borrowings. Legacy Banks also provides insurance and investment products and services, investment portfolio management, debit and credit card products and online banking. Its primary business includes residential and commercial real estate lending, small business loan and deposit services as well as variety of consumer loan and deposit services. At December 31, 2010, Legacy had total assets of $916.9 million, total deposits of $685.2 million and total stockholders’ equity of $111.6 million.

Special Meeting of Legacy Bancorp, Inc. Stockholders; Required Vote (page 30)

A special meeting of Legacy stockholders is scheduled to be held at _____________________, Pittsfield, Massachusetts at ____ p.m., local time, on [Date]. At the special meeting, you will be asked to vote on a proposal to approve the Merger Agreement between Legacy and Berkshire Hills. You may also be asked to vote to adjourn the special meeting, if necessary, to permit further solicitation of proxies if there are not sufficient votes at the time of the meeting to approve the Merger Agreement.

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Only Legacy stockholders of record as of the close of business on [Record Date] are entitled to notice of, and to vote at, the Legacy special meeting and any adjournments or postponements of the meeting.

Approval of the Merger Agreement requires the affirmative vote of holders of a majority of the outstanding shares of Legacy common stock entitled to vote. As of the record date, there were _________ shares of Legacy common stock outstanding and entitled to vote. The directors and executive officers of Legacy, as a group, beneficially owned _______ shares of Legacy common stock, representing ____% of the outstanding shares of Legacy common stock as of the record date and have agreed to vote their shares in favor of the Merger at the special meeting.

Special Meeting of Berkshire Hills Bancorp, Inc. Stockholders; Required Vote (page 32)

A special meeting of Berkshire Hills stockholders is scheduled to be held at _____________________, Pittsfield, Massachusetts at ____ p.m., local time, on [Date]. At the special meeting, you will be asked to vote on a proposal to approve the Merger Agreement between Legacy and Berkshire Hills, and an amendment to the Berkshire Hills Certificate of Incorporation to increase the number of authorized shares of common stock from 26 million to 50 million. You may also be asked to vote to adjourn the special meeting, if necessary, to permit further solicitation of proxies if there are not sufficient votes at the time of the meeting to approve the Merger Agreement or the amendment to the Berkshire Hills Certificate of Incorporation.

Only Berkshire Hills stockholders of record as of the close of business on [Record Date] are entitled to notice of, and to vote at, the Berkshire Hills special meeting and any adjournments or postponements of the meeting.

Approval of the Merger Agreement requires the affirmative vote of holders of a majority of the outstanding shares of Berkshire Hills common stock entitled to vote. Under the Berkshire Hills Certificate of Incorporation and Bylaws and Delaware law, the amendment of Berkshire Hills Certificate of Incorporation requires a vote “FOR” the amendment by a majority of the outstanding Common Stock entitled to vote thereof. As of the record date, there were _________ shares of Berkshire Hills common stock outstanding. The directors and executive officers of Berkshire Hills, as a group, beneficially owned _______ shares of Berkshire Hills common stock, representing ____% of the outstanding shares of Berkshire Hills common stock as of the record date.

The Merger and the Merger Agreement (page 38)

Berkshire Hills’ acquisition of Legacy is governed by the Merger Agreement. The Merger Agreement provides that, if all of the conditions are satisfied or waived, Legacy will be merged with and into Berkshire Hills with Berkshire Hills as the surviving entity.We encourage you to read the Merger Agreement, which is included as Appendix A to this Joint Proxy Statement/Prospectus.

What Legacy Bancorp, Inc. Stockholders Will Receive in the Merger (page 66)

Under the Merger Agreement, each share of Legacy common stock will be exchanged for 0.56385 shares of Berkshire Hills common stock and $1.30 in cash. If Berkshire Hills and Legacy must divest deposit liabilities in order to comply with a requirement contained in any regulatory approval, and if the weighted average deposit premium that Berkshire Hills receives for those divested deposits exceeds 350 basis points, then Berkshire Hills will be required under the Merger Agreement to make an additional cash payment to Legacy stockholders that, in the aggregate, will equal 50% of the premium in excess of 350 basis points (net of applicable taxes on such excess premium). Such payment would occur following completion of any such divestiture, which is anticipated to occur after completion of the Merger.

Comparative Market Prices (page 66)

The following table shows the closing price per share of Berkshire Hills common stock and the equivalent price per share of Legacy common stock, giving effect to the Merger, on December 21, 2010, which is the last day on which shares of Berkshire Hills common stock traded preceding the public announcement of the proposed Merger, and on [Record Date], the most recent practicable date prior to the mailing of this Joint Proxy Statement/Prospectus. The equivalent price per share of Legacy common stock was

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computed by multiplying the price of a share of Berkshire Hills common stock by the 0.56385 exchange ratio. The equivalent price per share of Legacy common stock does not include the $1.30 cash portion of the Merger Consideration. See “Description of the Merger — Consideration to be Received in the Merger” on page 66.

		Berkshire Hills Bancorp, Inc. Common Stock				Equivalent Price Per Share of Legacy Bancorp, Inc. Common Stock
December 21, 2010		$				$
[Record Date]		$				$

Recommendation of Legacy Bancorp, Inc. Board of Directors (page 47)

The Legacy board of directors has unanimously approved the Merger Agreement and the proposed merger. The Legacy board believes that the Merger Agreement, including the Merger contemplated by the Merger Agreement, is fair to, and in the best interests of, Legacy and its stockholders, and thereforeunanimously recommends that Legacy stockholders vote “FOR” the proposal to approve the Merger Agreement. In its reaching this decision, Legacy’s board of directors considered a variety of factors, which are described in the section captioned “Description of the Merger — Recommendation of the Legacy Board of Directors; Legacy’s Reasons for the Merger” beginning on page 47.

The Legacy board of directors unanimously recommends that Legacy stockholders vote“FOR” the proposal to adjourn the special meeting to a later date or dates, if necessary, to permit further solicitation of proxies if there are not sufficient votes at the time of the special meeting to approve the Merger Agreement.

Opinion of Legacy Bancorp, Inc.’s Financial Advisor (page 50)

In deciding to approve the Merger, one of the factors considered by Legacy’s board of directors was the opinion of KBW, which served as financial advisor to Legacy’s board of directors. KBW delivered its oral opinion on December 21, 2010, which was confirmed in writing on December 21, 2010, that the Merger consideration is fair to the holders of Legacy common stock from a financial point of view. The full text of this opinion is included as Appendix B to the Joint Proxy Statement/Prospectus. You should read the opinion carefully to understand the procedures followed, assumptions made, matters considered and limitations of the review conducted by KBW. Legacy has agreed to pay KBW a fee equal to 1.25 percent of the aggregate purchase price contingent upon completion of the Merger for its services in connection with the Merger. KBW has received a fee of $200,000 for the rendering of its fairness opinion, which fee shall be credited against the 1.25 percent fee referenced above if the Merger is completed.

Recommendation of Berkshire Hills Bancorp, Inc. Board of Directors (page 57)

The Berkshire Hills board of directors has unanimously approved the Merger Agreement and the proposed merger. The Berkshire Hills board believes that the Merger Agreement, including the Merger contemplated by the Merger Agreement, is fair to, and in the best interests of, Berkshire Hills and its stockholders, and thereforeunanimously recommends that Berkshire Hillsstockholders vote “FOR” the proposal to approve the Merger Agreement. In its reaching this decision, Berkshire Hill’s board of directors considered a variety of factors, which are described in the section captioned “Description of the Merger — Recommendation of Berkshire Hills Bancorp, Inc. Board of Directors and Reasons for the Merger” beginning on page 57.

The Berkshire Hills board of directors has unanimously approved the amendment to the Certificate of Incorporation to increase the amount of authorized common stock from 26 million to 50 million. The Berkshire Hills board believes that the proposed amendment to the Certificate of Incorporation is in the best interests of Berkshire Hills and its stockholders, and thereforeunanimously recommends that Berkshire Hills stockholders vote “FOR” the proposal to amend a Certificate of Incorporation.

The Berkshire Hills board of directors unanimously recommends that Berkshire Hills stockholders vote “FOR” the proposal to adjourn the special meeting to a later date or dates, if necessary, to permit further solicitation of proxies if there are not sufficient votes at the time of the special meeting to approve the Merger Agreement.

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Opinion of Berkshire Hills Bancorp, Inc.’s Financial Advisor (page 58)

In deciding to approve the Merger, one of the factors considered by Berkshire Hills’ board of directors was the opinion of Sandler O’Neill, which served as financial advisor to Berkshire Hills’ board of directors. Sandler O’Neill delivered its oral opinion on December 20, 2010, which was confirmed in writing on December 21, 2010, that the Merger consideration is fair to the holders of Berkshire Hills common stock from a financial point of view. The full text of this opinion is included as Appendix C to the Joint Proxy Statement/Prospectus. You should read the opinion carefully to understand the procedures followed, assumptions made, matters considered and limitations of the review conducted by Sandler O’Neill. Berkshire Hills has agreed to pay Sandler O’Neill a transaction fee of $810,000, of which $162,000 was paid upon the signing of the Merger Agreement and the remainder to be paid upon completion of the Merger. Sandler O’Neill also received a fee of $150,000 for the rendering of its fairness opinion.

Regulatory Matters Relating to the Merger (page 71)

Under the terms of the Merger Agreement, the Merger cannot be completed unless it is first approved by the Office of Thrift Supervision, the Massachusetts Division of Banks, the Massachusetts Board of Bank Incorporation and the Federal Deposit Insurance Corporation. Berkshire Hills has filed the required applications. As of the date of this document, Berkshire Hills has not received any approvals from those regulators. While Berkshire Hills does not know of any reason why it would not be able to obtain approval in a timely manner, Berkshire Hills cannot be certain when or if it will receive regulatory approval. As part of its regulatory filings, Berkshire Hills has requested the bank regulators and the United States Department of Justice to authorize Berkshire Hills and Legacy to divest approximately $162.0 million in deposits as well as four Legacy branch offices located in Berkshire County, Massachusetts. There can be no assurance as to whether the bank regulators or the United States Department of Justice will accept, deny or modify the proposed divestiture plan.

Conditions to Completing the Merger (page 78)

The completion of the Merger is subject to the fulfillment of a number of conditions, including:

Terminating the Merger Agreement (page 84)

The Merger Agreement may be terminated by mutual consent of Berkshire Hills and Legacy at any time prior to the completion of the Merger. Additionally, subject to conditions and circumstances described in the Merger Agreement, either Berkshire Hills or Legacy may terminate the Merger Agreement if, among other things, any of the following occur:

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Legacy also may terminate the Merger Agreement if Berkshire Hills’ stock price falls below thresholds set forth in the Merger Agreement and Berkshire Hills does not increase the exchange ratio pursuant to a prescribed formula.

Berkshire Hills may also terminate the Merger Agreement if Legacy materially breaches its agreements regarding the solicitation of other acquisition proposals and the submission of the Merger Agreement to stockholders or if the board of directors of Legacy does not recommend approval of the Merger in the Joint Proxy Statement/Prospectus or withdraws or revises its recommendation in a manner adverse to Berkshire Hills.

Termination Fee (page 85)

Under certain circumstances described in the Merger Agreement, Berkshire Hills may demand from Legacy Bancorp, Inc. a $4,320,000 termination fee in connection with the termination of the Merger Agreement. See “Description of the Merger — Termination Fee” on page 85 for a list of the circumstances under which a termination fee is payable.

Interests of Certain Persons in the Merger that are Different from Yours (page 73)

In considering the recommendation of the board of directors of Legacy to adopt the Merger Agreement, you should be aware that officers and directors of Legacy have employment and other compensation agreements or plans that give them interests in the Merger that are somewhat different from, or in addition to, their interests as Legacy stockholders. These interests and agreements, which provide for cash payments in the aggregate amount of approximately $___ million, include:

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Accounting Treatment of the Merger (page 68)

The Merger will be accounted for using the acquisition method in accordance with U.S. generally accepted accounting principles.

Comparison of Rights of Stockholders (page 89)

When the Merger is completed, Legacy stockholders who are to receive shares of Berkshire Hills will become Berkshire Hills stockholders and their rights will be governed by Delaware law and by Berkshire Hills’ certificate of incorporation and bylaws. See “Comparison of Rights of Stockholders” beginning on page 89 for a summary of the material differences between the respective rights of Legacy and Berkshire Hills stockholders.

Rights of Dissenting Stockholders (page 34)

Legacy stockholders have dissenters’ rights and may receive payment in cash of the fair value of their shares, excluding any appreciation in value that results from the merger. To maintain its dissenters’ rights a stockholder must (1) deliver written notice of its intent to demand payment for its shares to Legacy Bancorp, Inc. before the special meeting of Legacy stockholders or at the special meeting but before the vote is taken and (2) either vote against the merger or not submit a proxy. See “Rights of Dissenting Stockholders” on page 34.

Legacy stockholders may dissent from the Merger and, upon complying with the requirements of Delaware law, receive cash in the amount of the fair value of their shares instead of shares of Berkshire Hills common stock and/or the cash consideration specified in the Merger Agreement. A copy of the section of the Delaware General Corporation Law pertaining to dissenters’ rights is attached as Appendix D to this Joint Proxy Statement/Prospectus.You should read the statute carefully and consult with your legal counsel if you intend to exercise these rights.

Material Tax Consequences of the Merger (page 68)

Provided that the merger will qualify as a tax-free reorganization for United States federal income tax purposes, since Legacy stockholders will receive a combination of Berkshire Hills common stock and cash, Legacy stockholders may recognize gain, but not any loss, on the exchange of their stock for Berkshire Hills common stock and cash. For a more detailed discussion of the material United States federal income tax consequences of the transaction, including the tax consequences of the aggregate divestiture premium (described on pages 68 and 70) that may be paid to Legacy stockholders as additional cash consideration for such stockholders’ shares of Legacy common stock, please see the section “Description of the Merger — Material Tax Consequences of the Merger” beginning on page 68.

This tax treatment may not apply to all Legacy stockholders. Determining the actual tax consequences of the Merger to Legacy stockholders can be complicated. Legacy stockholders should consult their own tax advisor for a full understanding of the Merger’s tax consequences that are particular to each stockholder.

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RISK FACTORS

In addition to the other information contained in or incorporated by reference into this Joint Proxy Statement/Prospectus, you should consider carefully the risk factors described below, in deciding how to vote. You should keep these risk factors in mind when you read forward-looking statements in this document. Please refer to the section of this Joint Proxy Statement/Prospectus titled “Caution About Forward-Looking Statements” beginning on page 11.

The price of Berkshire Hills common stock will fluctuate, and therefore Legacy stockholders will not know until the effective time of the Merger the value of the consideration they will receive in the Merger.

Because the per share stock consideration is fixed at 0.56385 shares of Berkshire Hills common stock, the market value of the Berkshire Hills common stock to be issued in the Merger will depend upon the market price of Berkshire Hills common stock. This market price likely will vary from the closing price of Berkshire Hills common stock on the date the Merger was announced, on the date that this proxy statement/prospectus was mailed, and on the date of the Berkshire Hills or Legacy special meeting. Accordingly, at the time of the Legacy special meeting, Legacy stockholders will not necessarily know or be able to calculate the value of the stock consideration they would be entitled to receive upon completion of the Merger. You should obtain current market quotations for shares of Berkshire Hills common stock and for shares of Legacy common stock.

The price of Berkshire Hills common stock might decrease after the Merger.

Following the Merger, holders of Legacy common stock will become stockholders of Berkshire Hills. Berkshire Hills common stock could decline in value after the Merger. For example, during the twelve-month period ending on [Record Date] (the most recent practicable date before the printing of this Joint Proxy Statement/Prospectus), the price of Berkshire Hills common stock varied from a low of $_____ to a high of $_____ and ended that period at $_____. The market value of Berkshire Hills common stock fluctuates based upon general market conditions, Berkshire Hills’ business and prospects and other factors. Further, the market price of Berkshire Hills common stock after the merger may be affected by factors different from those affecting the common stock of Berkshire Hills or Legacy currently. The businesses of Legacy and Berkshire Hills differ and, accordingly, the results of operations of the combined company and the market price of the combined company’s shares of common stock may be affected by factors different from those currently affecting the independent results of operations and market prices of common stock of each of Legacy and Berkshire Hills. For a discussion of the businesses of Legacy and Berkshire Hills and of certain factors to consider in connection with those businesses, see the documents incorporated by reference in this proxy statement/prospectus and referred to under “Where You Can Find More Information” beginning on page 96.

Berkshire Hills may be unsuccessful in pursuing a plan to divest certain deposits and other liabilities. Such proposed divestiture plan may constitute a material adverse effect on the parties.

Berkshire Hills and Legacy are both headquartered in Pittsfield, Massachusetts, and, as a result, each bank has a significant number of branches and deposit market share in and around their headquarters and the surrounding area. Berkshire Hills and Legacy have among the largest deposit market shares in the Pittsfield market area. As part of its regulatory filings, Berkshire Hills has requested the bank regulators and the United States Department of Justice to authorize Berkshire Hills and Legacy to divest approximately $162.0 million in deposits, as well as four Legacy branch offices located in Berkshire County, Massachusetts. There can be no assurance as to whether the bank regulators or the United States Department of Justice will accept, deny or modify the proposed divestiture plan, or the timing of such approvals.

In addition, any regulatory approval that includes a requirement that the parties divest more than $200.0 million of deposit liabilities, whether from Legacy, Berkshire Hills or a combination of the two, together with related branch premises and loans, may be considered a material adverse effect as defined in the Merger Agreement, and therefore be cause to terminate the Merger Agreement.

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There can be no assurance that any amount will be paid to Legacy stockholders in respect of divested deposit liabilities.

If Berkshire Hills and Legacy must divest deposit liabilities in order to comply with a requirement contained in any regulatory approval, and if the weighted average deposit premium that Berkshire Hills receives for those divested deposits exceeds 350 basis points, then Berkshire Hills will be required under the Merger Agreement to make an additional cash payment to Legacy stockholders that, in the aggregate, will equal 50% of the premium in excess of 350 basis points (net of applicable taxes on such excess premium). The right to such payment is not transferable. Such payment would occur following completion of any such divestiture, which is anticipated to occur after completion of the Merger. However, there can be no assurance that Berkshire Hills will be required to divest deposit liabilities. Additionally, in the event Berkshire Hills is required to do so, there can be no assurance that the weighted average deposit premium that Berkshire Hills receives for those divested deposits will exceed 350 basis points and the Legacy stockholders will receive any payment with respect to such divested deposit liabilities.

Berkshire Hills may be unable to successfully integrate Legacy’s operations and retain Legacy’s employees.

The Merger involves the integration of two companies that have previously operated independently. The difficulties of combining the operations of the two companies include:

The process of integrating operations could cause an interruption of, or loss of momentum in, the activities of the business and the loss of key personnel. The integration of the two companies will require the experience and expertise of certain key employees of Legacy who are expected to be retained by Berkshire Hills. Berkshire Hills may not be successful in retaining these employees for the time period necessary to successfully integrate Legacy’s operations with those of Berkshire Hills. The diversion of management’s attention and any delay or difficulty encountered in connection with the Merger and the integration of the two companies’ operations could have an adverse effect on the business and results of operation of Berkshire Hills following the Merger.

The termination fee and the restrictions on solicitation contained in the Merger Agreement may discourage other companies from trying to acquire Legacy

Until the completion of the Merger, with some exceptions, Legacy is prohibited from soliciting, initiating, encouraging or participating in any discussion of or otherwise considering any inquiry or proposal that may lead to an acquisition proposal, such as a merger or other business combination transaction, with any person other than Berkshire Hills. In addition, Legacy has agreed to pay a termination fee to Berkshire Hills in specified circumstances. These provisions could discourage other companies from trying to acquire Legacy even though those other companies might be willing to offer greater value to Legacy’s stockholders than Berkshire Hills has offered in the Merger. The payment of the termination fee could also have a material adverse effect on Legacy’s financial condition. Legacy was afforded the opportunity to solicit additional acquisition proposals from third parties from the date of the Merger Agreement until January 31, 2011, which resulted in no other offers being made to Legacy.

Certain of Legacy’s officers and directors have interests that are different from, or in addition to, interests of Legacy stockholders generally.

You should be aware that the directors and officers of Legacy have interests in the Merger that are different from, or in addition to, the interests of Legacy stockholders generally. These include: two current Legacy board members joining the Berkshire Hills board of directors upon completion of the Merger; severance payments that certain officers will receive under existing employment or change-in-control agreements, the offer of executive-level employment that the President of Legacy will become subject to upon completion of the Merger; a non-competition and consulting agreement entered into with the Chief Executive Officer of Legacy; the payment for stock options; and provisions in the Merger Agreement relating to

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indemnification of directors and officers and insurance for directors and officers of Legacy for events occurring before the Merger. For a more detailed discussion of these interests, see “Description of the Merger — Interests of Certain Persons in the Merger that are Different from Yours” beginning on page 73.

Failure to complete the Merger could negatively impact the stock prices and future businesses and financial results of Berkshire Hills and Legacy

If the Merger is not completed, the ongoing businesses of Berkshire Hills and Legacy may be adversely affected and Berkshire Hills and Legacy will be subject to several risks, including the following:

In addition, if the Merger is not completed, Berkshire Hills and/or Legacy may experience negative reactions from the financial markets and from their respective customers and employees. This risk may be particularly significant since the parties share the same primary market area. Berkshire Hills and/or Legacy also could be subject to litigation related to any failure to complete the Merger or to enforcement proceedings commenced against Berkshire Hills or Legacy to perform their respective obligations under the Merger Agreement. If the Merger is not completed, Berkshire Hills and Legacy cannot assure their stockholders that the risks described above will not materialize and will not materially affect the business, financial results and stock prices of Berkshire Hills and/or Legacy.

Legacy stockholders will have a reduced ownership and voting interest after the Merger and will exercise less influence over management of the combined organization.

Legacy stockholders currently have the right to vote in the election of the Legacy Board of Directors and on various other matters affecting Legacy. Upon the completion of the Merger, each Legacy stockholder will become a stockholder of Berkshire Hills with a percentage ownership of the combined organization that is much smaller than the stockholder’s percentage ownership of Legacy. It is expected that the former stockholders of Legacy as a group will receive shares in the merger constituting approximately [__]% of the outstanding shares of Berkshire Hills common stock immediately after the Merger. As a result, Legacy stockholders will have significantly less influence on the management and policies of Berkshire Hills than they now have on the management and policies of Legacy.

The shares of Berkshire Hills common stock to be received by Legacy stockholders receiving the stock consideration as a result of the Merger will have different rights from shares of Legacy common stock.

Following completion of the Merger, Legacy stockholders who receive the stock consideration will no longer be stockholders of Legacy but will instead be stockholders of Berkshire Hills. Although Legacy and Berkshire Hills each are incorporated under Delaware law, there will be important differences between the current rights of Legacy stockholders and the rights of Berkshire Hills stockholders that may be important to Legacy stockholders. See “Comparison of Rights of Stockholders” beginning on page 89 for a discussion of the different rights associated with Berkshire Hills common stock and Legacy common stock.

The fairness opinion obtained by Legacy from its financial advisor does not reflect changes in circumstances subsequent to the date of the fairness opinion

KBW, Legacy’s financial advisor in connection with the Merger, has delivered to the board of directors of Legacy its opinion dated as of December 21, 2010. The opinion of KBW stated that as of such date, and based upon and subject to the factors and assumptions set forth therein, the Merger consideration to be paid to the holders of the outstanding shares of Legacy common stock pursuant to the Merger Agreement was fair

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from a financial point of view to such holders. The opinion does not reflect changes that may occur or may have occurred after the date of the opinion, including changes to the operations and prospects of Berkshire Hills or Legacy, changes in general market and economic conditions or regulatory or other factors. Any such changes, or changes in other factors on which the opinion is based, may materially alter or affect the relative values of Berkshire Hills and Legacy.

The fairness opinion obtained by Berkshire Hills from its financial advisor does not reflect changes in circumstances subsequent to the date of the fairness opinion

Sandler O’Neill, Berkshire Hills’s financial advisor in connection with the Merger, has delivered to the board of directors of Berkshire Hills its opinion dated as of December 21, 2010. The opinion of Sandler O’Neill stated that as of such date, and based upon and subject to the factors and assumptions set forth therein, the Merger consideration to be paid to the holders of the outstanding shares of Berkshire Hills common stock pursuant to the Merger Agreement was fair from a financial point of view to such holders. The opinion does not reflect changes that may occur or may have occurred after the date of the opinion, including changes to the operations and prospects of Legacy or Berkshire Hills, changes in general market and economic conditions or regulatory or other factors. Any such changes, or changes in other factors on which the opinion is based, may materially alter or affect the relative values of Legacy and Berkshire Hills.

There is no assurance when or even if the Merger will be completed.

Completion of the Merger is subject to satisfaction or waiver of a number of conditions. See “Description of the Merger — Conditions to Completing the Merger” on page 78. There can be no assurance that Berkshire Hills and Legacy will be able to satisfy the closing conditions or that closing conditions beyond their control will be satisfied or waived.

Berkshire Hills and Legacy can agree at any time to terminate the Merger Agreement, even if Legacy stockholders and Berkshire Hills stockholders have already voted to approve the merger agreement. Berkshire Hills and Legacy can also terminate the Merger Agreement under other specified circumstances.

The Merger is subject to the receipt of consents and approvals from regulatory authorities that may impose conditions that could have an adverse effect on Berkshire Hills or, if not obtained, could prevent completion of the Merger.

Before the Merger may be completed, various approvals and consents must be obtained from regulatory entities. These regulators may impose conditions on the completion of the Merger or require changes to the terms of the Merger. Any such conditions or changes could have the effect of delaying completion of the Merger or imposing additional costs on or limiting the revenues of Berkshire Hills following the Merger. In addition, pending elimination of the Office of Thrift Supervision and transfer of its responsibilities to other federal banking agencies may adversely affect the timely processing of the applications.

Either Berkshire Hills or Legacy may terminate the Merger Agreement if the Merger has not been completed by November 30, 2011, unless the failure of the merger to be completed has resulted from the failure of the party seeking to terminate the merger agreement to perform its obligations under the Merger Agreement.

Any failure to successfully integrate the businesses of Rome and Legacy or otherwise realize the expected benefits from Berkshire Hills’ recent mergers could adversely affect Berkshire Hills’ results of operations or financial condition.

There are significant risks and uncertainties associated with mergers and acquisitions. The success of Berkshire Hills’ mergers with Rome and Legacy will depend, in part, on Berkshire Hills’ ability to realize the anticipated benefits and cost savings from combining the businesses of Berkshire Hills with Rome and Legacy. If Berkshire Hills is are not able to successfully integrate these businesses, the anticipated benefits and cost savings of the acquisitions may not be realized fully or may take longer to realize than expected. For example, Berkshire Hills may fail to realize the growth opportunities and cost savings anticipated to be derived from the acquisition. In addition, as with regard to any of acquisition, a significant decline in asset valuations or cash flows may also cause Berkshire Hills not to realize expected benefits.

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To the extent that the purchase price, consisting of cash plus the number of shares of Berkshire Hills common stock issued or to be issued in the Rome and Legacy mergers, exceeds the fair value of the net assets, including identifiable intangibles of Rome and Legacy, at the respective merger dates, that amount will be reported as goodwill. In accordance with current accounting guidance, goodwill will not be amortized but will be evaluated for impairment annually. A failure to realize expected benefits of the Rome or Legacy merger could adversely impacting the carrying value of the goodwill recognized in those mergers, and in turn negatively affect Berkshire Hills’ financial condition.

CAUTION ABOUT FORWARD-LOOKING STATEMENTS

Certain statements contained in this document that are not historical facts may constitute forward-looking statements within the meaning of Section 27A of the Securities Act of 1933, as amended (referred to as the Securities Act), and Section 21E of the Securities Exchange Act of 1934, as amended (referred to as the Securities Exchange Act), and are intended to be covered by the safe harbor provisions of the Private Securities Litigation Reform Act of 1995. The sections of this document which contain forward-looking statements include, but are not limited to, “Questions And Answers About the Merger and the Special Meeting,” “ Summary,” “Risk Factors,” “Description of the Merger — Background of the Merger,” “Description of the Merger — Legacy’s 2011 Management Financial Projections,” and “Description of the Merger — Recommendation of the Legacy Board of Directors; Legacy’s Reasons for the Merger.” You can identify these statements from the use of the words “may,” “will,” “should,” “could,” “would,” “plan,” “potential,” “estimate,” “project,” “believe,” “intend,” “anticipate,” “expect,” “target” and similar expressions.

These forward-looking statements are subject to significant risks, assumptions and uncertainties, including among other things, changes in general economic and business conditions and the risks and other factors set forth in the “Risk Factors” section beginning on page 7.

Additional factors that could cause the results of Berkshire Hills or Legacy to differ materially from those described in the forward-looking statements can be found in the filings made by Berkshire Hill and Legacy with the Securities and Exchange Commission, including the Berkshire Hills Annual Report on Form 10-K for the fiscal year ended December 31, 2010 and the Legacy Annual Report on Form 10-K for the fiscal year ended December 31, 2010.

Because of these and other uncertainties, Berkshire Hills’ actual results, performance or achievements, or industry results, may be materially different from the results indicated by these forward-looking statements. In addition, Berkshire Hills’ and Legacy’s past results of operations do not necessarily indicate Berkshire Hills’ and Legacy’s combined future results. You should not place undue reliance on any of the forward-looking statements, which speak only as of the dates on which they were made. Neither Berkshire Hills nor Legacy is undertaking an obligation to update these forward-looking statements, even though its situation may change in the future, except as required under federal securities law. Each of Berkshire Hills and Legacy qualifies all of its forward-looking statements by these cautionary statements.

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SELECTED HISTORICAL FINANCIAL INFORMATION

The following tables show summarized historical financial data for Berkshire Hills and Legacy. You should read this summary financial information in connection with Berkshire Hills’ historical financial information, which is incorporated by reference into this document, and in connection with Legacy’s historical financial information, which is incorporated by reference into this document.

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SELECTED HISTORICAL FINANCIAL AND OTHER DATA OF
BERKSHIRE HILLS BANCORP, INC.

		At December 31,
(In thousands, except per share data)		2010				2009				2008				2007				2006
Selected Financial Data:
Total assets		$	2,880,716			$	2,700,424			$	2,666,729			$	2,513,432			$	2,149,642
Loans(1)			2,142,162				1,961,658				2,007,152				1,944,016				1,698,987
Allowance for loan losses			(31,898	)			(31,816	)			(22,908	)			(22,116	)			(19,370	)
Securities			405,953				420,966				341,516				258,497				234,174
Goodwill and other intangible assets			173,079				176,100				178,830				182,452				121,341
Total deposits			2,204,441				1,986,762				1,829,580				1,822,563				1,521,938
Borrowings and subordinated debentures			260,301				306,668				374,621				349,938				360,469
Total stockholders’ equity			387,960				384,581				408,425				326,837				258,161
Non-performing loans			13,712				38,700				12,171				10,508				7,592

		For the Years Ended December 31,
		2010				2009				2008				2007				2006
Selected Operating Data:
Total interest and dividend income		$	112,277			$	115,476			$	133,211			$	131,944			$	118,051
Total interest expense			35,330				45,880				57,471				68,019				57,811
Net interest income			76,947				69,596				75,740				63,925				60,240
Service charges and fee income			29,859				28,181				30,334				26,654				13,539
All other non-interest income (loss)			1,300				808				1,261				(2,011	)			(1,491	)
Total non-interest income			31,159				28,989				31,595				24,643				12,048
Total net revenue			108,106				98,585				107,335				88,568				72,288
Provision for loan losses			8,526				47,730				4,580				4,300				7,860
Total non-interest expense			81,729				78,571				71,699				65,494				48,868
Income tax expense (benefit) – continuing operations			4,113				(11,649	)			8,812				5,239				4,668
Net income from discontinued operations			—				—				—				—				371
Net income (loss)			13,738				(16,067	)			22,244				13,535				11,263
Less: Cumulative preferred stock dividends and accretion			—				1,030				—				—				—
Less: Deemed dividend from preferred stock repayment			—				2,954				—				—				—
Net income (loss) available to common stockholders		$	13,738			$	(20,051	)		$	22,244			$	13,535			$	11,263

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		At or For the Years Ended December 31,
		2010				2009				2008				2007				2006
Selected Operating Ratios and Other Data:
Performance Ratios:
Return (loss) on average assets(2)			0.50	%			(0.60	)%			0.87	%			0.60	%			0.53	%
Return (loss) on average equity(3)			3.54				(3.90	)			6.47				4.69				4.40
Net interest rate spread (tax equivalent)(4)			3.00				2.61				3.06				2.79				2.81
Net interest margin (tax equivalent)(5)			3.27				3.00				3.44				3.26				3.24
Non-interest income/total net revenue			28.82				29.41				29.44				27.82				16.67
Non-interest expense/average assets			2.97				2.93				2.81				2.90				2.31
Efficiency ratio(6)			70.59				73.39				64.40				62.94				58.46
Capital Ratios:
Average equity/average assets			14.11				15.36				13.49				12.73				12.08
Equity/total assets			13.47				14.24				15.32				13.00				12.01
Tier 1 capital to average assets – Berkshire Bank			8.02				7.86				9.34				7.97				7.69
Total capital to risk-weighted assets – Berkshire Bank			10.58				10.71				12.28				10.40				10.27
Asset Quality Ratios:
Nonperforming assets/total assets			0.59				1.43				0.48				0.45				0.35
Nonperforming loans/total loans			0.64				1.97				0.61				0.54				0.45
Net loans charged-off/average total loans			0.42				1.96				0.19				0.34				0.07
Allowance for loan losses/nonperforming loans			233				82				188				210				255
Allowance for loan losses as a percent of loans			1.49				1.62				1.14				1.14				1.14
Share Data:
Basic earnings per common share		$	0.99			$	(1.52	)		$	2.08			$	1.47			$	1.32
Diluted earnings per common share			0.99				(1.52	)			2.06				1.44				1.29
Dividends per common share			0.64				0.64				0.63				0.58				0.56
Book value per share			27.56				27.64				30.33				31.15				29.63
Market price at year end			22.11				20.68				30.86				26.00				33.46
Weighted average common shares outstanding – basic			13,862				13,189				10,700				9,223				8,538
Weighted average common shares outstanding – diluted			13,896				13,189				10,791				9,370				8,730

Note: All performance ratios are based on average balance sheet amounts where applicable.

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SELECTED HISTORICAL FINANCIAL AND OTHER DATA OF LEGACY BANCORP, INC.

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		At or For the Years Ended December 31,
		2010				2009				2008				2007				2006
Selected Operating Ratios and Other Data:
Performance Ratios:
Return (loss) on average assets(2)			(0.84	)%			(0.82	)%			0.16	%			0.15	%			0.36	%
Return (loss) on average equity(3)			(6.48	)			(6.20	)			1.11				0.88				1.92
Net interest rate spread(4)			2.79				2.78				2.80				2.26				2.39
Net interest margin(5)			3.05				3.13				3.27				3.01				3.15
Efficiency ratio(6)			96.10				84.9				77.5				93.0				74.2
Non-interest expense to average assets			3.29				3.04				2.89				3.23				2.70
Dividend payout ratio			n/a				n/a				111.61				113.82				40.88
Capital Ratios:
Equity to total assets(7)			12.2	%			12.8	%			13.1	%			14.4	%			18.6	%
Average equity to average assets(7)			12.9				13.3				14.1				16.9				18.5
Total capital to risk-weighted assets – Bank			12.0				12.3				13.0				13.9				18.9
Asset Quality Ratios:
Nonperforming assets/total assets			1.63	%			2.20	%			0.80	%			0.17	%			0.11	%
Nonperforming loans/total loans			2.07				2.96				1.08				0.23				0.15
Allowance for loan losses/nonperforming loans			70.70				56.64				87.99				363.45				532.08
Allowance for loan losses/total loans			1.47				1.67				0.95				0.85				0.80
Share Data:
Earnings (loss per share)		$	(0.99	)		$	(0.98	)		$	0.18			$	0.14			$	0.29
Dividends per share		$	0.20			$	0.20			$	0.20			$	0.16			$	0.12
Book value per share – end of year		$	12.92			$	13.89			$	14.14			$	14.40			$	14.55
Market price at year end			13.14				9.86				10.68				13.26				15.85

n/a = Not Applicable

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UNAUDITED PRO FORMA COMBINED CONDENSED CONSOLIDATED FINANCIAL
INFORMATION RELATING TO THE ROME AND LEGACY MERGERS

The unaudited pro forma combined condensed consolidated financial information has been prepared using the acquisition method of accounting, giving effect to the merger of Berkshire Hills with Rome and the proposed merger with Legacy. The unaudited pro forma combined condensed consolidated statement of financial condition combines the historical financial information of Berkshire Hills, Rome, and Legacy as of December 31, 2010 and assumes that the mergers were completed on that date. The unaudited pro forma combined condensed consolidated statements of operations combine the historical financial information of Berkshire Hills, Rome, and Legacy and give effect to the mergers as if they had been completed as of January 1, 2010. The unaudited pro forma combined condensed consolidated financial information is presented for illustrative purposes only and is not necessarily indicative of the results of operations or financial condition had the mergers been completed on the dates described above, nor is it necessarily indicative of the results of operations in future periods or the future financial position of the combined entities. The financial information should be read in conjunction with the accompanying Notes to the Unaudited Pro Forma Combined Condensed Consolidated Financial Information. Certain reclassifications have been made to Rome's and Legacy’s historical financial information in order to conform to Berkshire Hills' presentation of financial information.

The actual value of Berkshire Hills common stock to be recorded as consideration in these mergers will be based on the closing price of Berkshire Hills common stock at the time of the merger completion dates. The merger with Rome was completed prior to the start of business on April 1, 2011; the closing price of Berkshire Hills’ stock on March 31, 2011 was $20.83, and that price was used to value Berkshire Hills’ stock. The proposed merger with Legacy is targeted for completion in the third quarter of 2011. There can be no assurance that the Legacy merger will be completed as anticipated. For purposes of the pro forma financial information, the fair value of Berkshire Hills common stock to be issued in connection with the Legacy merger was based on the $20.75 average closing price of the stock for the ten day period ending December 15, 2010, which was shortly prior to the date of the execution of the Agreement and Plan of Merger on December 21, 2010.

The pro forma financial information includes estimated adjustments, including adjustments to record assets and liabilities of Rome and Legacy at their respective fair values and represents the pro forma estimates by Berkshire Hills based on available fair value information as of the dates of the respective Agreements and Plans of Merger. In some cases, where noted, more recent information has been used to support estimated adjustments in the pro forma financial information.

The pro forma adjustments included herein are subject to change depending on changes in interest rates and the components of assets and liabilities and as additional information becomes available and additional analyses are performed. The final allocation of the purchase price for each merger will be determined after each merger is completed and after completion of thorough analyses to determine the fair value of Rome’s and Legacy’s tangible and identifiable intangible assets and liabilities as of the dates the mergers are completed. Increases or decreases in the estimated fair values of the net assets as compared with the information shown in the unaudited pro forma combined condensed consolidated financial information may change the amount of the purchase price allocated to goodwill and other assets and liabilities and may impact Berkshire Hills’ statement of operations due to adjustments in yield and/or amortization of the adjusted assets or liabilities. Any changes to Rome’s or Legacy’s stockholders’ equity, including results of operations from December 31, 2010 through the dates the mergers are completed, will also change the purchase price allocation, which may include the recording of a lower or higher amount of goodwill. The final adjustments may be materially different from the unaudited pro forma adjustments presented herein.

Berkshire Hills anticipates that the mergers with Rome and Legacy will provide the combined company with financial benefits that include reduced operating expenses. Berkshire Hills expects to realize cost savings approximating 35% of the anticipated non-interest expense of Rome and approximating 42% of the anticipated non-interest expense of Legacy These cost savings are not included in these pro forma statements and there can be no assurance that expected cost savings will be realized. The pro forma information, while helpful in illustrating the financial characteristics of the combined company under one set of assumptions, does not reflect the benefits of expected cost savings or opportunities to earn additional revenue and, accordingly, does

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not attempt to predict or suggest future results. It also does not necessarily reflect what the historical results of the combined company would have been had our companies been combined during these periods.

The unaudited pro forma combined condensed consolidated financial information has been derived from and should be read in conjunction with the historical consolidated financial statements and the related notes of Berkshire Hills, Rome, and Legacy, which are incorporated in this joint proxy statement/prospectus by reference. See “Where You Can Find More InformationRights of Dissenting Stockholders” on page 9434.

You alsoLegacy stockholders may request copies of these documentsdissent from Berkshire Hills Bancorp, Inc. Berkshire Hills Bancorp, Inc. will provide you with copies of these documents, without charge,the Merger and, upon written or oral request to:

Berkshire Hills Bancorp, Inc.
24 North Street
Pittsfield, Massachusetts 01201
Attention: Investor Relations Department
Telephone: (413) 236-3239

If you are a Rome Bancorp, Inc. stockholder and would like to request documents from Berkshire Hills Bancorp, Inc., please do so by ____________ to receive them before the Rome Bancorp, Inc. special meeting.

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QUESTIONS AND ANSWERS ABOUT THE MERGER AND THE SPECIAL MEETINGRISK FACTORS

In addition to the other information contained in or incorporated by reference into this Joint Proxy Statement/Prospectus, you should consider carefully the risk factors described below, in deciding how to vote. You should keep these risk factors in mind when you read forward-looking statements in this document. Please refer to the section of this Joint Proxy Statement/Prospectus titled “Caution About Forward-Looking Statements” beginning on page 11.

The price of Berkshire Hills common stock will fluctuate, and therefore Legacy stockholders will not know until the effective time of the Merger the value of the consideration they will receive in the Merger.

Because the per share stock consideration is fixed at 0.56385 shares of Berkshire Hills common stock, the market value of the Berkshire Hills common stock to be issued in the Merger will depend upon the market price of Berkshire Hills common stock. This market price likely will vary from the closing price of Berkshire Hills common stock on the date the Merger was announced, on the date that this proxy statement/prospectus was mailed, and on the date of the Berkshire Hills or Legacy special meeting. Accordingly, at the time of the Legacy special meeting, Legacy stockholders will not necessarily know or be able to calculate the value of the stock consideration they would be entitled to receive upon completion of the Merger. You should obtain current market quotations for shares of Berkshire Hills common stock and for shares of Legacy common stock.

The price of Berkshire Hills common stock might decrease after the Merger.

Following the Merger, holders of Legacy common stock will become stockholders of Berkshire Hills. Berkshire Hills common stock could decline in value after the Merger. For example, during the twelve-month period ending on [Record Date] (the most recent practicable date before the printing of this Joint Proxy Statement/Prospectus), the price of Berkshire Hills common stock varied from a low of $_____ to a high of $_____ and ended that period at $_____. The market value of Berkshire Hills common stock fluctuates based upon general market conditions, Berkshire Hills’ business and prospects and other factors. Further, the market price of Berkshire Hills common stock after the merger may be affected by factors different from those affecting the common stock of Berkshire Hills or Legacy currently. The businesses of Legacy and Berkshire Hills differ and, accordingly, the results of operations of the combined company and the market price of the combined company’s shares of common stock may be affected by factors different from those currently affecting the independent results of operations and market prices of common stock of each of Legacy and Berkshire Hills. For a discussion of the businesses of Legacy and Berkshire Hills and of certain factors to consider in connection with those businesses, see the documents incorporated by reference in this proxy statement/prospectus and referred to under “Where You Can Find More Information” beginning on page 96.

Berkshire Hills may be unsuccessful in pursuing a plan to divest certain deposits and other liabilities. Such proposed divestiture plan may constitute a material adverse effect on the parties.

Berkshire Hills and Legacy are both headquartered in Pittsfield, Massachusetts, and, as a result, each bank has a significant number of branches and deposit market share in and around their headquarters and the surrounding area. Berkshire Hills and Legacy have among the largest deposit market shares in the Pittsfield market area. As part of its regulatory filings, Berkshire Hills has requested the bank regulators and the United States Department of Justice to authorize Berkshire Hills and Legacy to divest approximately $162.0 million in deposits, as well as four Legacy branch offices located in Berkshire County, Massachusetts. There can be no assurance as to whether the bank regulators or the United States Department of Justice will accept, deny or modify the proposed divestiture plan, or the timing of such approvals.

In addition, any regulatory approval that includes a requirement that the parties divest more than $200.0 million of deposit liabilities, whether from Legacy, Berkshire Hills or a combination of the two, together with related branch premises and loans, may be considered a material adverse effect as defined in the Merger Agreement, and therefore be cause to terminate the Merger Agreement.

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There can be no assurance that any amount will be paid to Legacy stockholders in respect of divested deposit liabilities.

If Berkshire Hills and Legacy must divest deposit liabilities in order to comply with a requirement contained in any regulatory approval, and if the weighted average deposit premium that Berkshire Hills receives for those divested deposits exceeds 350 basis points, then Berkshire Hills will be required under the Merger Agreement to make an additional cash payment to Legacy stockholders that, in the aggregate, will equal 50% of the premium in excess of 350 basis points (net of applicable taxes on such excess premium). The right to such payment is not transferable. Such payment would occur following completion of any such divestiture, which is anticipated to occur after completion of the Merger. However, there can be no assurance that Berkshire Hills will be required to divest deposit liabilities. Additionally, in the event Berkshire Hills is required to do so, there can be no assurance that the weighted average deposit premium that Berkshire Hills receives for those divested deposits will exceed 350 basis points and the Legacy stockholders will receive any payment with respect to such divested deposit liabilities.

Berkshire Hills may be unable to successfully integrate Legacy’s operations and retain Legacy’s employees.

The Merger involves the integration of two companies that have previously operated independently. The difficulties of combining the operations of the two companies include:

The process of integrating operations could cause an interruption of, or loss of momentum in, the activities of the business and the loss of key personnel. The integration of the two companies will require the experience and expertise of certain key employees of Legacy who are expected to be retained by Berkshire Hills. Berkshire Hills may not be successful in retaining these employees for the time period necessary to successfully integrate Legacy’s operations with those of Berkshire Hills. The diversion of management’s attention and any delay or difficulty encountered in connection with the Merger and the integration of the two companies’ operations could have an adverse effect on the business and results of operation of Berkshire Hills following the Merger.

The termination fee and the restrictions on solicitation contained in the Merger Agreement may discourage other companies from trying to acquire Legacy

Until the completion of the Merger, with some exceptions, Legacy is prohibited from soliciting, initiating, encouraging or participating in any discussion of or otherwise considering any inquiry or proposal that may lead to an acquisition proposal, such as a merger or other business combination transaction, with any person other than Berkshire Hills. In addition, Legacy has agreed to pay a termination fee to Berkshire Hills in specified circumstances. These provisions could discourage other companies from trying to acquire Legacy even though those other companies might be willing to offer greater value to Legacy’s stockholders than Berkshire Hills has offered in the Merger. The payment of the termination fee could also have a material adverse effect on Legacy’s financial condition. Legacy was afforded the opportunity to solicit additional acquisition proposals from third parties from the date of the Merger Agreement until January 31, 2011, which resulted in no other offers being made to Legacy.

Certain of Legacy’s officers and directors have interests that are different from, or in addition to, interests of Legacy stockholders generally.

You should be aware that the directors and officers of Legacy have interests in the Merger that are different from, or in addition to, the interests of Legacy stockholders generally. These include: two current Legacy board members joining the Berkshire Hills board of directors upon completion of the Merger; severance payments that certain officers will receive under existing employment or change-in-control agreements, the offer of executive-level employment that the President of Legacy will become subject to upon completion of the Merger; a non-competition and consulting agreement entered into with the Chief Executive Officer of Legacy; the payment for stock options; and provisions in the Merger Agreement relating to

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indemnification of directors and officers and insurance for directors and officers of Legacy for events occurring before the Merger. For a more detailed discussion of these interests, see “Description of the Merger — Interests of Certain Persons in the Merger that are Different from Yours” beginning on page 73.

Failure to complete the Merger could negatively impact the stock prices and future businesses and financial results of Berkshire Hills and Legacy

If the Merger is not completed, the ongoing businesses of Berkshire Hills and Legacy may be adversely affected and Berkshire Hills and Legacy will be subject to several risks, including the following:

In addition, if the Merger is not completed, Berkshire Hills and/or Legacy may experience negative reactions from the financial markets and from their respective customers and employees. This risk may be particularly significant since the parties share the same primary market area. Berkshire Hills and/or Legacy also could be subject to litigation related to any failure to complete the Merger or to enforcement proceedings commenced against Berkshire Hills or Legacy to perform their respective obligations under the Merger Agreement. If the Merger is not completed, Berkshire Hills and Legacy cannot assure their stockholders that the risks described above will not materialize and will not materially affect the business, financial results and stock prices of Berkshire Hills and/or Legacy.

Legacy stockholders will have a reduced ownership and voting interest after the Merger and will exercise less influence over management of the combined organization.

Legacy stockholders currently have the right to vote in the election of the Legacy Board of Directors and on various other matters affecting Legacy. Upon the completion of the Merger, each Legacy stockholder will become a stockholder of Berkshire Hills with a percentage ownership of the combined organization that is much smaller than the stockholder’s percentage ownership of Legacy. It is expected that the former stockholders of Legacy as a group will receive shares in the merger constituting approximately [__]% of the outstanding shares of Berkshire Hills common stock immediately after the Merger. As a result, Legacy stockholders will have significantly less influence on the management and policies of Berkshire Hills than they now have on the management and policies of Legacy.

The shares of Berkshire Hills common stock to be received by Legacy stockholders receiving the stock consideration as a result of the Merger will have different rights from shares of Legacy common stock.

Following completion of the Merger, Legacy stockholders who receive the stock consideration will no longer be stockholders of Legacy but will instead be stockholders of Berkshire Hills. Although Legacy and Berkshire Hills each are incorporated under Delaware law, there will be important differences between the current rights of Legacy stockholders and the rights of Berkshire Hills stockholders that may be important to Legacy stockholders. See “Comparison of Rights of Stockholders” beginning on page 89 for a discussion of the different rights associated with Berkshire Hills common stock and Legacy common stock.

The fairness opinion obtained by Legacy from its financial advisor does not reflect changes in circumstances subsequent to the date of the fairness opinion

KBW, Legacy’s financial advisor in connection with the Merger, has delivered to the board of directors of Legacy its opinion dated as of December 21, 2010. The opinion of KBW stated that as of such date, and based upon and subject to the factors and assumptions set forth therein, the Merger consideration to be paid to the holders of the outstanding shares of Legacy common stock pursuant to the Merger Agreement was fair

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from a financial point of view to such holders. The opinion does not reflect changes that may occur or may have occurred after the date of the opinion, including changes to the operations and prospects of Berkshire Hills or Legacy, changes in general market and economic conditions or regulatory or other factors. Any such changes, or changes in other factors on which the opinion is based, may materially alter or affect the relative values of Berkshire Hills and Legacy.

The fairness opinion obtained by Berkshire Hills from its financial advisor does not reflect changes in circumstances subsequent to the date of the fairness opinion

Sandler O’Neill, Berkshire Hills’s financial advisor in connection with the Merger, has delivered to the board of directors of Berkshire Hills its opinion dated as of December 21, 2010. The opinion of Sandler O’Neill stated that as of such date, and based upon and subject to the factors and assumptions set forth therein, the Merger consideration to be paid to the holders of the outstanding shares of Berkshire Hills common stock pursuant to the Merger Agreement was fair from a financial point of view to such holders. The opinion does not reflect changes that may occur or may have occurred after the date of the opinion, including changes to the operations and prospects of Legacy or Berkshire Hills, changes in general market and economic conditions or regulatory or other factors. Any such changes, or changes in other factors on which the opinion is based, may materially alter or affect the relative values of Legacy and Berkshire Hills.

There is no assurance when or even if the Merger will be completed.

Completion of the Merger is subject to satisfaction or waiver of a number of conditions. See “Description of the Merger — Conditions to Completing the Merger” on page 78. There can be no assurance that Berkshire Hills and Legacy will be able to satisfy the closing conditions or that closing conditions beyond their control will be satisfied or waived.

Berkshire Hills and Legacy can agree at any time to terminate the Merger Agreement, even if Legacy stockholders and Berkshire Hills stockholders have already voted to approve the merger agreement. Berkshire Hills and Legacy can also terminate the Merger Agreement under other specified circumstances.

The Merger is subject to the receipt of consents and approvals from regulatory authorities that may impose conditions that could have an adverse effect on Berkshire Hills or, if not obtained, could prevent completion of the Merger.

Before the Merger may be completed, various approvals and consents must be obtained from regulatory entities. These regulators may impose conditions on the completion of the Merger or require changes to the terms of the Merger. Any such conditions or changes could have the effect of delaying completion of the Merger or imposing additional costs on or limiting the revenues of Berkshire Hills following the Merger. In addition, pending elimination of the Office of Thrift Supervision and transfer of its responsibilities to other federal banking agencies may adversely affect the timely processing of the applications.

Either Berkshire Hills or Legacy may terminate the Merger Agreement if the Merger has not been completed by November 30, 2011, unless the failure of the merger to be completed has resulted from the failure of the party seeking to terminate the merger agreement to perform its obligations under the Merger Agreement.

Any failure to successfully integrate the businesses of Rome and Legacy or otherwise realize the expected benefits from Berkshire Hills’ recent mergers could adversely affect Berkshire Hills’ results of operations or financial condition.

There are significant risks and uncertainties associated with mergers and acquisitions. The success of Berkshire Hills’ mergers with Rome and Legacy will depend, in part, on Berkshire Hills’ ability to realize the anticipated benefits and cost savings from combining the businesses of Berkshire Hills with Rome and Legacy. If Berkshire Hills is are not able to successfully integrate these businesses, the anticipated benefits and cost savings of the acquisitions may not be realized fully or may take longer to realize than expected. For example, Berkshire Hills may fail to realize the growth opportunities and cost savings anticipated to be derived from the acquisition. In addition, as with regard to any of acquisition, a significant decline in asset valuations or cash flows may also cause Berkshire Hills not to realize expected benefits.

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To the extent that the purchase price, consisting of cash plus the number of shares of Berkshire Hills common stock issued or to be issued in the Rome and Legacy mergers, exceeds the fair value of the net assets, including identifiable intangibles of Rome and Legacy, at the respective merger dates, that amount will be reported as goodwill. In accordance with current accounting guidance, goodwill will not be amortized but will be evaluated for impairment annually. A failure to realize expected benefits of the Rome or Legacy merger could adversely impacting the carrying value of the goodwill recognized in those mergers, and in turn negatively affect Berkshire Hills’ financial condition.

CAUTION ABOUT FORWARD-LOOKING STATEMENTS

Certain statements contained in this document that are not historical facts may constitute forward-looking statements within the meaning of Section 27A of the Securities Act of 1933, as amended (referred to as the Securities Act), and Section 21E of the Securities Exchange Act of 1934, as amended (referred to as the Securities Exchange Act), and are intended to be covered by the safe harbor provisions of the Private Securities Litigation Reform Act of 1995. The sections of this document which contain forward-looking statements include, but are not limited to, “Questions And Answers About the Merger and the Special Meeting,” “ Summary,” “Risk Factors,” “Description of the Merger — Background of the Merger,” “Description of the Merger — Legacy’s 2011 Management Financial Projections,” and “Description of the Merger — Recommendation of the Legacy Board of Directors; Legacy’s Reasons for the Merger.” You can identify these statements from the use of the words “may,” “will,” “should,” “could,” “would,” “plan,” “potential,” “estimate,” “project,” “believe,” “intend,” “anticipate,” “expect,” “target” and similar expressions.

These forward-looking statements are subject to significant risks, assumptions and uncertainties, including among other things, changes in general economic and business conditions and the risks and other factors set forth in the “Risk Factors” section beginning on page 7.

Additional factors that could cause the results of Berkshire Hills or Legacy to differ materially from those described in the forward-looking statements can be found in the filings made by Berkshire Hill and Legacy with the Securities and Exchange Commission, including the Berkshire Hills Annual Report on Form 10-K for the fiscal year ended December 31, 2010 and the Legacy Annual Report on Form 10-K for the fiscal year ended December 31, 2010.

Because of these and other uncertainties, Berkshire Hills’ actual results, performance or achievements, or industry results, may be materially different from the results indicated by these forward-looking statements. In addition, Berkshire Hills’ and Legacy’s past results of operations do not necessarily indicate Berkshire Hills’ and Legacy’s combined future results. You should not place undue reliance on any of the forward-looking statements, which speak only as of the dates on which they were made. Neither Berkshire Hills nor Legacy is undertaking an obligation to update these forward-looking statements, even though its situation may change in the future, except as required under federal securities law. Each of Berkshire Hills and Legacy qualifies all of its forward-looking statements by these cautionary statements.

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SELECTED HISTORICAL FINANCIAL INFORMATION

The following tables show summarized historical financial data for Berkshire Hills and Legacy. You should read this summary financial information in connection with Berkshire Hills’ historical financial information, which is incorporated by reference into this document, and in connection with Legacy’s historical financial information, which is incorporated by reference into this document.

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SELECTED HISTORICAL FINANCIAL AND OTHER DATA OF
BERKSHIRE HILLS BANCORP, INC.

		At December 31,
(In thousands, except per share data)		2010				2009				2008				2007				2006
Selected Financial Data:
Total assets		$	2,880,716			$	2,700,424			$	2,666,729			$	2,513,432			$	2,149,642
Loans(1)			2,142,162				1,961,658				2,007,152				1,944,016				1,698,987
Allowance for loan losses			(31,898	)			(31,816	)			(22,908	)			(22,116	)			(19,370	)
Securities			405,953				420,966				341,516				258,497				234,174
Goodwill and other intangible assets			173,079				176,100				178,830				182,452				121,341
Total deposits			2,204,441				1,986,762				1,829,580				1,822,563				1,521,938
Borrowings and subordinated debentures			260,301				306,668				374,621				349,938				360,469
Total stockholders’ equity			387,960				384,581				408,425				326,837				258,161
Non-performing loans			13,712				38,700				12,171				10,508				7,592

		For the Years Ended December 31,
		2010				2009				2008				2007				2006
Selected Operating Data:
Total interest and dividend income		$	112,277			$	115,476			$	133,211			$	131,944			$	118,051
Total interest expense			35,330				45,880				57,471				68,019				57,811
Net interest income			76,947				69,596				75,740				63,925				60,240
Service charges and fee income			29,859				28,181				30,334				26,654				13,539
All other non-interest income (loss)			1,300				808				1,261				(2,011	)			(1,491	)
Total non-interest income			31,159				28,989				31,595				24,643				12,048
Total net revenue			108,106				98,585				107,335				88,568				72,288
Provision for loan losses			8,526				47,730				4,580				4,300				7,860
Total non-interest expense			81,729				78,571				71,699				65,494				48,868
Income tax expense (benefit) – continuing operations			4,113				(11,649	)			8,812				5,239				4,668
Net income from discontinued operations			—				—				—				—				371
Net income (loss)			13,738				(16,067	)			22,244				13,535				11,263
Less: Cumulative preferred stock dividends and accretion			—				1,030				—				—				—
Less: Deemed dividend from preferred stock repayment			—				2,954				—				—				—
Net income (loss) available to common stockholders		$	13,738			$	(20,051	)		$	22,244			$	13,535			$	11,263

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		At or For the Years Ended December 31,
		2010				2009				2008				2007				2006
Selected Operating Ratios and Other Data:
Performance Ratios:
Return (loss) on average assets(2)			0.50	%			(0.60	)%			0.87	%			0.60	%			0.53	%
Return (loss) on average equity(3)			3.54				(3.90	)			6.47				4.69				4.40
Net interest rate spread (tax equivalent)(4)			3.00				2.61				3.06				2.79				2.81
Net interest margin (tax equivalent)(5)			3.27				3.00				3.44				3.26				3.24
Non-interest income/total net revenue			28.82				29.41				29.44				27.82				16.67
Non-interest expense/average assets			2.97				2.93				2.81				2.90				2.31
Efficiency ratio(6)			70.59				73.39				64.40				62.94				58.46
Capital Ratios:
Average equity/average assets			14.11				15.36				13.49				12.73				12.08
Equity/total assets			13.47				14.24				15.32				13.00				12.01
Tier 1 capital to average assets – Berkshire Bank			8.02				7.86				9.34				7.97				7.69
Total capital to risk-weighted assets – Berkshire Bank			10.58				10.71				12.28				10.40				10.27
Asset Quality Ratios:
Nonperforming assets/total assets			0.59				1.43				0.48				0.45				0.35
Nonperforming loans/total loans			0.64				1.97				0.61				0.54				0.45
Net loans charged-off/average total loans			0.42				1.96				0.19				0.34				0.07
Allowance for loan losses/nonperforming loans			233				82				188				210				255
Allowance for loan losses as a percent of loans			1.49				1.62				1.14				1.14				1.14
Share Data:
Basic earnings per common share		$	0.99			$	(1.52	)		$	2.08			$	1.47			$	1.32
Diluted earnings per common share			0.99				(1.52	)			2.06				1.44				1.29
Dividends per common share			0.64				0.64				0.63				0.58				0.56
Book value per share			27.56				27.64				30.33				31.15				29.63
Market price at year end			22.11				20.68				30.86				26.00				33.46
Weighted average common shares outstanding – basic			13,862				13,189				10,700				9,223				8,538
Weighted average common shares outstanding – diluted			13,896				13,189				10,791				9,370				8,730

Note: All performance ratios are based on average balance sheet amounts where applicable.

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SELECTED HISTORICAL FINANCIAL AND OTHER DATA OF LEGACY BANCORP, INC.