<SUBMISSION>
<ACCESSION-NUMBER>0001362310-09-008378
<TYPE>8-K
<PUBLIC-DOCUMENT-COUNT>2
<PERIOD>20090527
<ITEMS>1.02
<ITEMS>9.01
<FILING-DATE>20090529
<DATE-OF-FILING-DATE-CHANGE>20090529
<FILER>
<COMPANY-DATA>
<CONFORMED-NAME>BERKSHIRE HILLS BANCORP INC
<CIK>0001108134
<ASSIGNED-SIC>6036
<IRS-NUMBER>043510455
<FISCAL-YEAR-END>1231
</COMPANY-DATA>
<FILING-VALUES>
<FORM-TYPE>8-K
<ACT>34
<FILE-NUMBER>000-51584
<FILM-NUMBER>09861748
</FILING-VALUES>
<BUSINESS-ADDRESS>
<STREET1>24 NORTH ST.
<CITY>PITTSFIELD
<STATE>MA
<ZIP>01201
<PHONE>4134435601
</BUSINESS-ADDRESS>
<MAIL-ADDRESS>
<STREET1>24 NORTH ST
<CITY>PITTSFIELD
<STATE>MA
<ZIP>01201
</MAIL-ADDRESS>
</FILER>
<DOCUMENT>
<TYPE>8-K
<SEQUENCE>1
<FILENAME>c86278e8vk.htm
<DESCRIPTION>FORM 8-K
<TEXT>
<HTML>
<HEAD>
<TITLE>Form 8-K</TITLE>
</HEAD>
<BODY bgcolor="#FFFFFF">
<!-- PAGEBREAK -->
<DIV style="margin-left: 0.25in; width: 7.2in;font-family: 'Times New Roman',Times,serif">
<DIV style="width: 100%; border-bottom: 2pt solid black; font-size: 1pt">&nbsp;</DIV>
<DIV style="width: 100%; border-bottom: 1pt solid black; font-size: 1pt">&nbsp;</DIV>

<DIV align="center" style="font-size: 14pt; margin-top: 12pt"><B>UNITED STATES<BR>
SECURITIES AND EXCHANGE COMMISSION</B>
</DIV>

<DIV align="center" style="font-size: 12pt"><B>Washington, D.C. 20549</B>
</DIV>

<DIV align="center" style="font-size: 18pt; margin-top: 12pt"><B>FORM 8-K</B>
</DIV>

<DIV align="center" style="font-size: 12pt; margin-top: 12pt"><B>CURRENT REPORT<BR>
Pursuant to Section&nbsp;13 OR 15(d) of The Securities Exchange Act of 1934</B>
</DIV>

<DIV align="center" style="font-size: 10pt; margin-top: 12pt"><B>Date of Report (Date of earliest event reported): May 27, 2009</B></DIV>

<DIV align="center" style="font-size: 24pt; margin-top: 12pt"><B>BERKSHIRE HILLS BANCORP, INC.</B>
</DIV>

<DIV align="center" style="font-size: 10pt">(Exact name of registrant as specified in its charter)</DIV>

<DIV align="center">
<TABLE style="font-size: 10pt" cellspacing="0" border="0" cellpadding="0" width="100%">
<!-- Begin Table Head -->
<TR valign="bottom">
<TD width="32%">&nbsp;</TD>
<TD width="2%">&nbsp;</TD>
<TD width="32%">&nbsp;</TD>
<TD width="2%">&nbsp;</TD>
<TD width="32%">&nbsp;</TD>
</TR>
<!-- End Table Head -->
<!-- Begin Table Body -->
<TR valign="bottom">
<TD nowrap align="center" valign="top"><B>Delaware
</B></TD>
<TD>&nbsp;</TD>
<TD align="center" valign="top"><B>0-51584
</B></TD>
<TD>&nbsp;</TD>
<TD align="center" valign="top"><B>04-3510455</B></TD>
</TR>
<TR style="font-size: 1px">
<TD valign="top" align="left" style="border-top: 1px solid #000000">&nbsp;</TD>
<TD valign="top" align="left">&nbsp;</TD>
<TD valign="top" align="left" style="border-top: 1px solid #000000">&nbsp;</TD>
<TD valign="top" align="left">&nbsp;</TD>
<TD valign="top" align="left" style="border-top: 1px solid #000000">&nbsp;</TD>
</TR>
<TR valign="bottom">
<TD align="center" valign="top">(State or other jurisdiction<BR>
of incorporation)
</TD>
<TD>&nbsp;</TD>
<TD align="center" valign="top">(Commission File Number)
</TD>
<TD>&nbsp;</TD>
<TD align="center" valign="top">(IRS Employer Identification No.)</TD>
</TR>
<!-- End Table Body -->
</TABLE>
</DIV>

<DIV align="center">
<TABLE style="font-size: 10pt" cellspacing="0" border="0" cellpadding="0" width="100%">
<!-- Begin Table Head -->
<TR valign="bottom">
<TD width="48%">&nbsp;</TD>
<TD width="2%">&nbsp;</TD>
<TD width="48%">&nbsp;</TD>
</TR>
<!-- End Table Head -->
<!-- Begin Table Body -->
<TR valign="bottom">
<TD align="center" valign="top"><B>24 North Street,<BR>
Pittsfield, Massachusetts
</B></TD>
<TD>&nbsp;</TD>
<TD align="center" valign="top"><B>&nbsp;<BR>01201</B></TD>
</TR>
<TR style="font-size: 1px">
<TD valign="top" align="left" style="border-top: 1px solid #000000">&nbsp;</TD>
<TD valign="top" align="left">&nbsp;</TD>
<TD valign="top" align="left" style="border-top: 1px solid #000000">&nbsp;</TD>
</TR>
<TR valign="bottom">
<TD align="center" valign="top">(Address of principal executive offices)
</TD>
<TD>&nbsp;</TD>
<TD align="center" valign="top">(Zip Code)</TD>
</TR>
<!-- End Table Body -->
</TABLE>
</DIV>

<DIV align="center" style="font-size: 10pt; margin-top: 12pt">Registrant&#146;s telephone number, including area code: <B>(413) 443-5601</B></DIV>

<DIV align="center" style="font-size: 10pt; margin-top: 12pt"><B>Not Applicable</B></DIV>

<DIV align="center" style="font-size: 10pt"><FONT style="border-top: 1px solid #000000">(Former name or former address, if changed since last report.)</FONT></DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 6pt">Check the appropriate box below if the Form 8-K filing is intended to simultaneously satisfy the filing obligation of the registrant under any of the following provisions: </DIV>

<DIV style="margin-top: 6pt">
<TABLE width="100%" border="0" cellpadding="0" cellspacing="0" style="font-size: 10pt">

<TR valign="top" style="font-size: 10pt; color: #000000; background: transparent">
<TD width="3%" nowrap align="left"><FONT face="wingdings" size="2">&#111;</FONT></TD>
<TD width="1%">&nbsp;</TD>
<TD>Written communications pursuant to Rule&nbsp;425 under the Securities Act (17 CFR 230.425)</TD>
</TR>

<TR>
<TD style="font-size: 6pt">&nbsp;</TD>
</TR><TR valign="top" style="font-size: 10pt; color: #000000; background: transparent">
<TD width="3%" nowrap align="left"><FONT face="wingdings" size="2">&#111;</FONT></TD>
<TD width="1%">&nbsp;</TD>
<TD>Soliciting material pursuant to Rule&nbsp;14a-12 under the Exchange Act (17 CFR 240.14a-12)</TD>
</TR>

<TR>
<TD style="font-size: 6pt">&nbsp;</TD>
</TR><TR valign="top" style="font-size: 10pt; color: #000000; background: transparent">
<TD width="3%" nowrap align="left"><FONT face="wingdings" size="2">&#111;</FONT></TD>
<TD width="1%">&nbsp;</TD>
<TD>Pre-commencement communications pursuant to Rule&nbsp;14d-2(b) under the Exchange Act (17 CFR 240.14d-2(b))</TD>
</TR>

<TR>
<TD style="font-size: 6pt">&nbsp;</TD>
</TR><TR valign="top" style="font-size: 10pt; color: #000000; background: transparent">
<TD width="3%" nowrap align="left"><FONT face="wingdings" size="2">&#111;</FONT></TD>
<TD width="1%">&nbsp;</TD>
<TD>Pre-commencement communications pursuant to Rule&nbsp;13e-4(c) under the Exchange Act (17 CFR 240.13e-4(c))</TD>
</TR>

</TABLE>
</DIV>

<DIV style="width: 100%; border-bottom: 1pt solid black; margin-top: 10pt; font-size: 1pt">&nbsp;</DIV>
<DIV style="width: 100%; border-bottom: 2pt solid black; font-size: 1pt">&nbsp;</DIV>

<P align="center" style="font-size: 10pt"><!-- Folio --><!-- /Folio --> </DIV>
<!-- PAGEBREAK -->
<P><HR noshade><P>
<H5 align="left" style="page-break-before:always">&nbsp;</H5><P>
<DIV style="font-family: 'Times New Roman',Times,serif; margin-left: .25in; width: 7.20in">

<DIV align="left" style="font-size: 10pt; margin-top: 10pt"><B>Item&nbsp;1.02 </B><U><B>Termination of a Material Definitive Agreement. </B></U>
</DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 10pt; text-indent: 4%">On December&nbsp;19, 2008, Berkshire Hills Bancorp, Inc. (the &#147;Company&#148;) entered into a Letter
Agreement (the &#147;Purchase Agreement&#148;) with the United States Department of the Treasury (&#147;Treasury&#148;)
pursuant to which the Company issued and sold to Treasury: (i)&nbsp;40,000 shares of the Company&#146;s Fixed
Rate Cumulative Perpetual Preferred Stock, Series&nbsp;A, par value $0.01 per share (the &#147;Series&nbsp;A
Preferred Stock&#148;), having a liquidation amount per share equal to $1,000, for a total price of
$40,000,000, (ii)&nbsp;and a warrant (the &#147;Warrant&#148;) to purchase 226,330 shares of the Company&#146;s common
stock, par value $0.01 per share (the &#147;Common Stock&#148;), at an exercise price of $26.51.
</DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 10pt; text-indent: 4%">On May&nbsp;27, 2009, the Company redeemed the Series&nbsp;A Preferred Stock and returned to the
Treasury a total of $40,066,666.67, which includes the original investment amount of $40,000,000
plus accrued but unpaid dividends of $66,666.67. The return of the investment had the effect of
terminating the Company&#146;s continuing obligations under the Purchase Agreement, which agreement is
now terminated. The Letter of Transmittal for the redemption of the Series&nbsp;A Preferred Stock is
attached as Exhibit&nbsp;10.1 hereto and is incorporated herein by reference.
</DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 10pt; text-indent: 4%">The Company expects to notify the Treasury of its intent to repurchase the outstanding Warrant
for 226,330 shares of its common stock, subject to an agreed-upon negotiated repurchase price.
</DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 10pt; text-indent: 4%">During the period of its investment in the preferred stock of the Company, the Treasury
received cash dividends equal to a 5% annualized dividend rate on its investment. Additionally,
the Treasury will earn a profit on the anticipated repurchase of the associated warrant which the
Treasury received as partial consideration for its investment in the preferred stock.
</DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 10pt"><B>Item&nbsp;9.01.
</B><U><B>Financial Statements and Exhibits.</B></U>
</DIV>



<DIV align="left" style="font-size: 10pt; margin-top: 10pt; margin-left: 4%">(a)&nbsp;Not Applicable.
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 10pt; margin-left: 4%">(b)&nbsp;Not Applicable.
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 10pt; margin-left: 4%">(c)&nbsp;Not Applicable.
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 10pt; margin-left: 4%">(d)&nbsp;Exhibits.
</DIV>
<DIV align="center">
<TABLE style="font-size: 10pt" cellspacing="0" border="0" cellpadding="0" width="100%">
<!-- Begin Table Head --><TR valign="bottom">
    <TD width="5%">&nbsp;</TD>
    <TD width="1%">&nbsp;</TD>
    <TD width="5%">&nbsp;</TD>
    <TD width="3%">&nbsp;</TD>
    <TD width="77%">&nbsp;</TD>
</TR>
<TR style="font-size: 10pt" valign="bottom">
    <TD nowrap align="center" colspan="3" style="border-bottom: 1px solid #000000"><B>Exhibit No.</B></TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="left" style="border-bottom: 1px solid #000000"><B>Description</B></TD>
</TR>

<!-- End Table Head -->
<!-- Begin Table Body -->
<TR valign="bottom"><!-- Blank Space -->
    <TD nowrap align="right" valign="top">&nbsp;</TD>
    <TD align="right" valign="top">&nbsp;</TD>
    <TD valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
</TR>
<TR valign="bottom" style="padding-top: 1px">
    <TD nowrap align="right" valign="top">&nbsp;</TD>
    <TD align="right" valign="top">10.1</TD>
    <TD nowrap valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">Letter of Transmittal, dated May&nbsp;27, 2009, between the United States Department
of the Treasury and Berkshire Hills Bancorp, Inc.</DIV></TD>
</TR>
<!-- End Table Body --></TABLE>
</DIV>


<P align="center" style="font-size: 10pt">&nbsp;

<P align="center" style="font-size: 10pt"><!-- Folio -->&nbsp;<!-- /Folio -->
</DIV>

<!-- PAGEBREAK -->
<P><HR noshade><P>
<H5 align="left" style="page-break-before:always">&nbsp;</H5><P>

<DIV style="font-family: 'Times New Roman',Times,serif; margin-left: .25in; width: 7.20in">

<DIV align="center" style="font-size: 10pt; margin-top: 10pt"><B>SIGNATURES</B>
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 10pt; text-indent: 4%">Pursuant to the requirements of the Securities Exchange Act of 1934, the Registrant has duly
caused this report to be signed on its behalf by the undersigned, hereunto duly authorized.
</DIV>

<TABLE width="100%" border="0" cellspacing="0" cellpadding="0" style="font-size: 10pt">
<TR>
    <TD width="48%">&nbsp;</TD>
    <TD width="1%">&nbsp;</TD>
    <TD width="1%">&nbsp;</TD>
    <TD width="35%">&nbsp;</TD>
    <TD width="15%">&nbsp;</TD>
</TR>
<TR>
    <TD valign="top" align="left">&nbsp;</TD>
    <TD colspan="3" align="left"><B>BERKSHIRE HILLS BANCORP, INC.</B><BR>
&nbsp;</TD>
    <TD>&nbsp;</TD>
</TR><TR>
    <TD align="left">DATE: May 29, 2009&nbsp;</TD>
    <TD valign="top">By:&nbsp;&nbsp;</TD>
    <TD colspan="2" style="border-bottom: 1px solid #000000" align="left">/s/ Kevin P. Riley
&nbsp;</TD>
    <TD>&nbsp;</TD>
</TR><TR>
    <TD align="left">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD colspan="2" align="left">Kevin P. Riley&nbsp;</TD>
    <TD>&nbsp;</TD>
</TR><TR>
    <TD align="left">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD colspan="2" align="left" nowrap>Executive Vice President and Chief Financial
Officer&nbsp;</TD>
    <TD>&nbsp;</TD>
</TR>

</TABLE>

<P align="center" style="font-size: 10pt">&nbsp;

<P align="center" style="font-size: 10pt"><!-- Folio -->&nbsp;<!-- /Folio -->
</DIV>

<!-- PAGEBREAK -->
<P><HR noshade><P>
<H5 align="left" style="page-break-before:always">&nbsp;</H5><P>

<DIV style="font-family: 'Times New Roman',Times,serif; margin-left: .25in; width: 7.20in">

<TABLE width="100%" border="0" cellspacing="0" cellpadding="0" style="font-size: 10pt">
<TR>
    <TD width="48%">&nbsp;</TD>
    <TD width="1%">&nbsp;</TD>
    <TD width="1%">&nbsp;</TD>
    <TD width="35%">&nbsp;</TD>
    <TD width="15%">&nbsp;</TD>
</TR>

</TABLE>

<DIV align="center" style="font-size: 10pt; margin-top: 10pt"><B>EXHIBIT INDEX</B>
</DIV>

<DIV align="center">
<TABLE style="font-size: 10pt" cellspacing="0" border="0" cellpadding="0" width="100%">
<!-- Begin Table Head --><TR valign="bottom">
    <TD width="5%">&nbsp;</TD>
    <TD width="1%">&nbsp;</TD>
    <TD width="5%">&nbsp;</TD>
    <TD width="3%">&nbsp;</TD>
    <TD width="77%">&nbsp;</TD>
</TR>
<TR style="font-size: 10pt" valign="bottom">
    <TD nowrap align="center" colspan="3" style="border-bottom: 1px solid #000000"><B>Exhibit No.</B></TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="left" style="border-bottom: 1px solid #000000"><B>Description</B></TD>
</TR>

<!-- End Table Head -->
<!-- Begin Table Body -->
<TR valign="bottom"><!-- Blank Space -->
    <TD nowrap align="right" valign="top">&nbsp;</TD>
    <TD align="right" valign="top">&nbsp;</TD>
    <TD valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
</TR>
<TR valign="bottom" style="padding-top: 1px">
    <TD nowrap align="right" valign="top">&nbsp;</TD>
    <TD align="right" valign="top">10.1</TD>
    <TD nowrap valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">Letter of Transmittal, dated May&nbsp;27, 2009, between the United States Department
of the Treasury and Berkshire Hills Bancorp, Inc.</DIV></TD>
</TR>
<!-- End Table Body --></TABLE>
</DIV>



<P align="center" style="font-size: 10pt">&nbsp;

<P align="center" style="font-size: 10pt"><!-- Folio -->&nbsp;<!-- /Folio -->
</DIV>



</BODY>
</HTML>
</TEXT>
</DOCUMENT>
<DOCUMENT>
<TYPE>EX-10.1
<SEQUENCE>2
<FILENAME>c86278exv10w1.htm
<DESCRIPTION>EXHIBIT 10.1
<TEXT>
<HTML>
<HEAD>
<TITLE>Exhibit 10.1</TITLE>
</HEAD>
<BODY bgcolor="#FFFFFF">
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<DIV style="font-family: 'Times New Roman',Times,serif; margin-left: .25in; width: 7.20in">

<DIV align="right" style="font-size: 10pt; margin-top: 10pt"><B>Exhibit&nbsp;10.1</B>
</DIV>


<DIV align="center" style="font-size: 10pt; margin-top: 10pt">UNITED STATES DEPARTMENT OF THE TREASURY<BR>
1500 Pennsylvania Avenue, NW<BR>
Washington, D.C. 20220
</DIV>


<DIV align="center" style="font-size: 10pt; margin-top: 10pt">April&nbsp;8, 2009
</DIV>


<DIV align="justify" style="font-size: 10pt; margin-top: 10pt">Ladies and Gentlemen:
</DIV>

<DIV align="justify" style="font-size: 10pt; margin-top: 10pt; text-indent: 4%">Reference is made to that certain Letter Agreement incorporating the Securities Purchase
Agreement &#151; Standard Terms (the <I>&#147;Securities Purchase Agreement&#148;), </I>dated as of the date set forth on
Schedule&nbsp;A hereto, between the United States Department of the Treasury (the <I>&#147;Investor&#148;) </I>and the
company set forth on Schedule&nbsp;A hereto (the <I>&#147;Company&#148;). </I>Capitalized terms used but not defined
herein shall have the meanings assigned to them in the Securities Purchase Agreement. Pursuant to
the Securities Purchase Agreement , at the Closing, the Company issued to the Investor the number
of shares of the series of its preferred stock set forth on Schedule&nbsp;A hereto (the <I>&#147;Preferred
Shares&#148;) </I>and a warrant to purchase the number of shares of its common stock set forth on Schedule&nbsp;A
hereto (the <I>&#147;Warrant&#148;).</I>
</DIV>

<DIV align="justify" style="font-size: 10pt; margin-top: 10pt">
</DIV>


<DIV align="justify" style="font-size: 10pt; margin-top: 10pt; text-indent: 4%">In
connection with the consummation of the repurchase (the <I>&#147;Repurchase&#148;) </I>by the
Company from the Investor, on the date hereof, of the number of Preferred Shares listed on
Schedule&nbsp;A hereto (the <I>&#147;Repurchased Preferred Shares&#148;), </I>as permitted by the Emergency Economic
Stabilization Act of 2008 , as amended by the American Recovery and Reinvestment Act of 2009:
</DIV>


<DIV align="justify" style="font-size: 10pt; margin-top: 10pt; margin-left: 4%; text-indent: 4%">(a)&nbsp;The Company hereby acknowledges receipt from the Investor of the share
certificate(s) set forth on Schedule&nbsp;A hereto representing the Preferred Shares; and
</DIV>


<DIV align="justify" style="font-size: 10pt; margin-top: 10pt; margin-left: 4%; text-indent: 4%">(b)&nbsp;The Investor hereby acknowledges receipt from the Company of a wire transfer to
the account of the Investor set forth on Schedule&nbsp;A hereto in immediately available funds
of the aggregate purchase price set forth on Schedule&nbsp;A hereto, representing payment in
full for the Repurchased Preferred Shares at a price per share equal to the Liquidation
Amount per share, together with any accrued and unpaid dividends to, but excluding, the
date hereof.
</DIV>

<DIV align="justify" style="font-size: 10pt; margin-top: 10pt; text-indent: 4%">The Investor and the Company hereby agree that, notwithstanding Section&nbsp;4.4 of the Securities
Purchase Agreement, immediately following consummation of the Repurchase, but subject to compliance
with applicable securities laws, the Investor shall be permitted to Transfer all or a portion of
the Warrant or Substitute Warrant (as defined below) with respect to, and/or exercise the Warrant
or Substitute Warrant for, all or a portion of the number of shares of Common Stock issuable
thereunder, at any time and without limitation, and Section&nbsp;4.4 of the Securities Purchase
Agreement shall be deemed to be amended in order to permit the foregoing. The Company shall take
all steps as may be reasonably requested by the Investor to facilitate any such Transfer.
</DIV>
<DIV align="justify" style="font-size: 10pt; margin-top: 10pt; text-indent: 0%">UST
Seq. No. 200</div>

<P align="center" style="font-size: 10pt; text-indent: 4%">&nbsp;

<P align="center" style="font-size: 10pt"><!-- Folio -->&nbsp;<!-- /Folio -->
</DIV>

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<P><HR noshade><P>
<H5 align="left" style="page-break-before:always">&nbsp;</H5><P>

<DIV style="font-family: 'Times New Roman',Times,serif; margin-left: .25in; width: 7.20in">

<DIV align="justify" style="font-size: 10pt; margin-top: 10pt; text-indent: 4%">In addition, the Company agrees that within 15 calendar days of the date hereof the Company
shall either (a)&nbsp;deliver to the Investor a notice of intent to repurchase the Warrant in accordance
with Section&nbsp;4.9(b) of the Securities Purchase Agreement (the <I>&#147;Warrant Repurchase Notice&#148;), </I>or (b)
issue and deliver to the Investor a new warrant, in substantially the form of the Warrant, except
with the deletion of Section&nbsp;13(H) thereof, to purchase the number of shares of Common Stock into
which the Warrant is then exercisable (the <I>&#147;Substitute Warrant&#148;), </I>which Substitute Warrant shall be
deemed the <I>&#147;Warrant&#148; </I>for all purposes under the Securities Purchase Agreement.
</DIV>

<DIV align="justify" style="font-size: 10pt; margin-top: 10pt; text-indent: 4%">In the event that the Company delivers a Warrant Repurchase Notice and the Company and the
Investor fail to agree on the Fair Market Value of the Warrant pursuant to the procedures
(including the Appraisal Procedure), and in accordance with the time periods, set forth in Section
4.9(c) of the Securities Purchase Agreement or the Company revokes the delivery of such Warrant
Repurchase Notice, then the Company shall deliver a Substitute Warrant to the Investor within 5
calendar days of the earlier of the failure to agree on the Fair Market Value and the revocation of
the Warrant Repurchase Notice.
</DIV>

<DIV align="justify" style="font-size: 10pt; margin-top: 10pt; text-indent: 4%">Effective as of the date of receipt of the Substitute Warrant, if applicable, the Investor
hereby provides notice, pursuant to Section&nbsp;4.5(p) of the Securities Purchase Agreement, of its
intention to sell the Substitute Warrant.
</DIV>

<DIV align="justify" style="font-size: 10pt; margin-top: 10pt; text-indent: 4%">This letter agreement will be governed by and construed in accordance with the federal law of
the United States if and to the extent such law is applicable, and otherwise in accordance with the
laws of the State of New York applicable to contracts made and to be performed entirely within such
State.
</DIV>

<DIV align="justify" style="font-size: 10pt; margin-top: 10pt; text-indent: 4%">This letter agreement may be executed in any number of separate counterparts, each such
counterpart being deemed to be an original instrument, and all such counterparts will together
constitute the same agreement. Executed signature pages to this letter agreement may be delivered
by facsimile and such facsimiles will be deemed sufficient as if actual signature pages had been
delivered.
</DIV>

<DIV align="center" style="font-size: 10pt; margin-top: 10pt"><I>&#091;Remainder of this page intentionally left blank&#093;</I>
</DIV>

<DIV align="justify" style="font-size: 10pt; margin-top: 10pt; text-indent: 0%">UST
Seq. No. 200</div>

<P align="center" style="font-size: 10pt">&nbsp;

<P align="center" style="font-size: 10pt"><!-- Folio -->-2-<!-- /Folio -->
</DIV>

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<H5 align="left" style="page-break-before:always">&nbsp;</H5><P>

<DIV style="font-family: 'Times New Roman',Times,serif; margin-left: .25in; width: 7.20in">



<DIV align="justify" style="margin-top: 10pt; margin-right:1%; font-size: 10pt; text-indent: 4%">In witness whereof, the parties have duly executed this letter agreement as of the date
first written above.
</DIV>

<TABLE width="100%" border="0" cellspacing="0" cellpadding="0" style="font-size: 10pt">
<TR>
    <TD width="48%">&nbsp;</TD>
    <TD width="1%">&nbsp;</TD>
    <TD width="1%">&nbsp;</TD>
    <TD width="35%">&nbsp;</TD>
    <TD width="15%">&nbsp;</TD>
</TR>
<TR>
    <TD valign="top" align="left">&nbsp;</TD>
    <TD colspan="3" align="left">UNITED STATES DEPARTMENT OF THE TREASURY<BR>
&nbsp;</TD>
    <TD>&nbsp;</TD>
</TR><TR>
    <TD align="left">&nbsp;</TD>
    <TD valign="top">By:&nbsp;&nbsp;</TD>
    <TD colspan="2" style="border-bottom: 1px solid #000000" align="left">/s/ Duane Morse
&nbsp;</TD>
    <TD>&nbsp;</TD>
</TR><TR>
    <TD align="left">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD valign="top">Name:&nbsp;&nbsp;</TD>
    <TD align="left">Duane Morse&nbsp;</TD>
    <TD>&nbsp;</TD>
</TR><TR>
    <TD align="left">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD valign="top">Title:&nbsp;&nbsp;</TD>
    <TD align="left">Chief Risk and Compliance Officer&nbsp;</TD>
    <TD>&nbsp;</TD>
</TR>
<TR>
    <TD colspan="5">&nbsp;</TD>
</TR>
<TR>
    <TD valign="top" align="left">&nbsp;</TD>
    <TD colspan="3" align="left">BERKSHIRE HILLS BANCORP, INC.<BR>
&nbsp;</TD>
    <TD>&nbsp;</TD>
</TR><TR>
    <TD align="left">&nbsp;</TD>
    <TD valign="top">By:&nbsp;&nbsp;</TD>

<TD colspan="2" style="border-bottom: 1px solid #000000" align="left">/s/
Kevin P. Riley</TD>
    <TD>&nbsp;</TD>
</TR><TR>
    <TD align="left">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD valign="top">Name:&nbsp;&nbsp;</TD>
    <TD align="left" style="border-bottom: 0px solid #000000">Kevin P. Riley</TD>
    <TD>&nbsp;</TD>
</TR><TR>
    <TD align="left">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD valign="top">Title:&nbsp;&nbsp;</TD>

<TD align="left" style="border-bottom: 0px solid #000000">Executive
Vice President and CFO</TD>
    <TD>&nbsp;</TD>
</TR>
<TR>
    <TD colspan="5">&nbsp;</TD>
</TR>
</TABLE>


<DIV align="justify" style="font-size: 10pt; margin-top: 10pt; text-indent: 0%">UST
Seq. No. 200</div>

<P align="center" style="font-size: 10pt">&nbsp;

<P align="center" style="font-size: 10pt"><!-- Folio -->&nbsp;<!-- /Folio -->
</DIV>

<!-- PAGEBREAK -->
<P><HR noshade><P>
<H5 align="left" style="page-break-before:always">&nbsp;</H5><P>

<DIV style="font-family: 'Times New Roman',Times,serif; margin-left: .25in; width: 7.20in">

<DIV align="right" style="font-size: 10pt; margin-top: 10pt"><B>SCHEDULE A</B>
</DIV>


<DIV align="justify" style="font-size: 10pt; margin-top: 10pt"><U>General Information:</U>
</DIV>



<DIV align="justify" style="font-size: 10pt; margin-top: 10pt; margin-left: 4%">Date of Letter Agreement incorporating the
Securities Purchase Agreement: December 19, 2008
</DIV>


<DIV align="justify" style="font-size: 10pt; margin-top: 10pt; margin-left: 4%">Name
of the Company: Berkshire Hills Bancorp, Inc.
</DIV>


<DIV align="justify" style="font-size: 10pt; margin-top: 10pt; margin-left: 4%">Corporate or other organizational form of the
Company: Corporation
</DIV>


<DIV align="justify" style="font-size: 10pt; margin-top: 10pt; margin-left: 4%">Jurisdiction of organization of the Company:
Delaware
</DIV>


<DIV align="justify" style="font-size: 10pt; margin-top: 10pt; margin-left: 4%">Number and series of preferred stock issued to
the
Investor at the Closing: 40,000 shares of Fixed
Rate Cumulative Perpetual Preferred Stock, Series
A
</DIV>


<DIV align="justify" style="font-size: 10pt; margin-top: 10pt; margin-left: 4%">Number of Initial Warrant Shares: 226,330
</DIV>

<DIV align="justify" style="font-size: 10pt; margin-top: 10pt"><U>Terms of the Repurchase:</U>
</DIV>



<DIV align="justify" style="font-size: 10pt; margin-top: 10pt; margin-left: 4%">Number of Preferred Shares repurchased by
the Company: 40,000 (100%)
</DIV>


<DIV align="justify" style="font-size: 10pt; margin-top: 10pt; margin-left: 4%">Share certificate number (representing the
Preferred Shares previously issued to the
Investor at the Closing): No.&nbsp;1
</DIV>


<DIV align="justify" style="font-size: 10pt; margin-top: 10pt; margin-left: 4%">Per share Liquidation Amount of Preferred
Shares: $1,000
</DIV>


<DIV align="justify" style="font-size: 10pt; margin-top: 10pt; margin-left: 4%">Accrued and unpaid dividends on Preferred
Shares: $66,666.67
</DIV>


<DIV align="justify" style="font-size: 10pt; margin-top: 10pt; margin-left: 4%"><U>Aggregate
purchase price for Repurchased
Preferred Shares</U>: $40,066,666.67
</DIV>


<DIV align="justify" style="font-size: 10pt; margin-top: 10pt; margin-left: 4%">&#091;Difference between the Preferred Shares and the
Repurchased Preferred Shares:]<SUP>3</SUP> N/A
</DIV>
<DIV align="center">
<TABLE style="font-size: 10pt" cellspacing="0" border="0" cellpadding="0" width="100%">
<!-- Begin Table Head --><TR valign="bottom">
    <TD width="48%">&nbsp;</TD>
    <TD width="1%">&nbsp;</TD>
    <TD width="31%">&nbsp;</TD>
    <TD width="1%">&nbsp;</TD>
    <TD width="9%">&nbsp;</TD>
    <TD width="1%">&nbsp;</TD>
    <TD width="9%">&nbsp;</TD>
</TR>

<!-- End Table Head -->
<!-- Begin Table Body -->
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px"><B>Investor wire information for payment of purchase price:</B>
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top" colspan="4"><B>ABA Number:</B> 021000018
</TD>
    <TD nowrap valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom" style="padding-top: 1px">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top" colspan="5"><B>Bank: </B>The Bank
of New York Mellon
</TD>

</TR>
<TR valign="bottom" style="padding-top: 1px">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top" colspan="5"><B>Account Name:</B> BETA EESA Preferred Account
</TD>
</TR>
<TR valign="bottom" style="padding-top: 1px">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top" colspan="5"><B>Account Number:</B>
GLA/111567
</TD>
</TR>
<TR valign="bottom" style="padding-top: 1px">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top" colspan="3"><B>Beneficiary:</B> a/c #629904
</TD>
    <TD nowrap valign="top">&nbsp;</TD>
</TR>
<!-- End Table Body --></TABLE>
</DIV>



<DIV align="left">
<DIV style="font-size: 3pt; margin-top: 16pt; width: 18%; border-top: 1px solid #000000">&nbsp;</DIV>
</DIV>
<TABLE width="100%" border="0" cellpadding="0" cellspacing="0" style="font-size: 10pt">
<TR style="font-size: 3pt">
    <TD width="3%">&nbsp;</TD>
    <TD width="1%">&nbsp;</TD>
    <TD width="96">&nbsp;</TD>
</TR>
<TR valign="top">

<TD nowrap align="left"><SUP style="font-size: 85%; vertical-align: text-top">3</sup></TD>
    <TD>&nbsp;</TD>
    <TD><DIV style="text-align: justify">Bracketed cell to be included if the Company is repurchasing less than 100% of the
Preferred Shares issued at Closing.</DIV></TD>
</TR>

</TABLE>


<P align="center" style="font-size: 10pt">&nbsp;

<P align="center" style="font-size: 10pt"><!-- Folio -->&nbsp;<!-- /Folio -->
</DIV>

</BODY>
</HTML>
</TEXT>
</DOCUMENT>
</SUBMISSION>
