SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549

                                    FORM 11-K

                                  ANNUAL REPORT
                        PURSUANT TO SECTION 15(d) OF THE
                         SECURITIES EXCHANGE ACT OF 1934

[x]  ANNUAL REPORT  PURSUANT TO SECTION 15(d) OF THE SECURITIES  EXCHANGE ACT OF
     1934 [NO FEE REQUIRED, EFFECTIVE OCTOBER 7, 1996].

For the fiscal year ended           December 31, 2008
                           ---------------------------------------------------

                                       OR

[ ]  TRANSITION  REPORT  PURSUANT TO SECTION 15(d) OF THE SECURITIES  EXCHANGE
     ACT OF 1934 [NO FEE REQUIRED].

For the transition period from _______________ to  ______________________

                     Commission File Number 001-51584

     A. Full title of the plan and the address of the plan,  if  different  from
that of the issuer named below:

                           Berkshire Bank 401(k) Plan

     B: Name of  issuer  of the  securities  held  pursuant  to the plan and the
address of its principal executive office:

                          Berkshire Hills Bancorp, Inc.
                                  24 North St.
                              Pittsfield, MA 01201












                           Berkshire Bank 401(k) Plan








                 Financial Statements and Supplemental Schedule
                     Years Ended December 31, 2008 and 2007





                                    CONTENTS

                           BERKSHIRE BANK 401(k) PLAN


                 Financial Statements and Supplemental Schedule
                     Years Ended December 31, 2008 and 2007




The following financial information is submitted herewith:                 Page

       Report of Independent Registered Public Accounting Firm               1

       Statements of Net Assets Available for Benefits                       2

       Statements of Changes in Net Assets Available for Benefits            3

       Notes to Financial Statements                                      4-12

       Schedule H, Line 4i - Schedule of Assets
            (Held at End of Year)                                           13









             REPORT OF INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM




The Audit Committee
Berkshire Hills Bancorp, Inc.
Pittsfield, Massachusetts


We have audited the accompanying statements of net assets available for benefits
of Berkshire Bank 401(k) Plan (the "Plan") as of December 31, 2008 and 2007, and
the related  statements of changes in net assets  available for benefits for the
years then ended.  These  financial  statements  are the  responsibility  of the
Plan's  management.  Our  responsibility  is to  express  an  opinion  on  these
financial statements based on our audits.

We conducted our audits in accordance with the auditing  standards of the Public
Company Accounting Oversight Board (United States). Those standards require that
we plan and perform the audit to obtain  reasonable  assurance about whether the
financial  statements  are free of  material  misstatement.  An  audit  includes
examining,  on a test basis,  evidence supporting the amounts and disclosures in
the  financial  statements.  An audit also  includes  assessing  the  accounting
principles  used  and  significant  estimates  made  by  management,  as well as
evaluating the overall  financial  statement  presentation.  We believe that our
audits provide a reasonable basis for our opinion.

In our opinion,  the financial  statements  referred to above present fairly, in
all material  respects,  the net assets available for benefits of the Plan as of
December 31, 2008 and 2007, and the changes in net assets available for benefits
for the years then ended,  in conformity with  accounting  principles  generally
accepted in the United States of America.

Our  audits  were  made for the  purpose  of  forming  an  opinion  on the basic
financial statements taken as a whole. The supplemental schedule of assets (held
at year end) as of December 31, 2008 is presented  for the purpose of additional
analysis and is not a required part of the basic  financial  statements,  but is
supplementary  information  required by the United  States  Department  of Labor
Rules and Regulations for Reporting and Disclosure under the Employee Retirement
Income Security Act of 1974. This supplemental schedule is the responsibility of
the Plan's  management.  The  supplemental  schedule  has been  subjected to the
auditing procedures applied in the audit of the basic financial  statements and,
in our opinion,  is fairly  stated in all  material  respects in relation to the
basic financial statements taken as a whole.

/s/ Wolf & Company, P.C.

Boston, Massachusetts
June 24, 2009







                           BERKSHIRE BANK 401(k) PLAN

                 STATEMENTS OF NET ASSETS AVAILABLE FOR BENEFITS

                     Years Ended December 31, 2008 and 2007




                                                                              2008                  2007
                                                                      ------------------    ------------------
ASSETS
                                                                                            
Cash and cash equivalents                                                   $ 4,333,973           $ 3,385,352
Investments, at fair value                                                   27,364,015            38,345,382
Participant loans                                                               539,452               746,559
                                                                      ------------------    ------------------
                                                                             32,237,440            42,477,293
                                                                      ------------------    ------------------
Receivables:
   Employer contributions                                                             -                52,410
   Participant contributions                                                          -                56,624
                                                                      ------------------    ------------------
                                                                                      -               109,034
                                                                      ------------------    ------------------
                       Net assets available for benefits                    $32,237,440           $42,586,327
                                                                      ==================    ==================





See accompanying notes to financial statements.

                                       2




                           BERKSHIRE BANK 401(k) PLAN

           STATEMENTS OF CHANGES IN NET ASSETS AVAILABLE FOR BENEFITS

                     Years Ended December 31, 2008 and 2007



                                                                                   2008                2007
                                                                             ------------------  ------------------
Additions to net assets attributed to:
Investment income:
                                                                                                 
Interest and dividends                                                             $ 1,167,954         $ 1,408,238
                                                                             ------------------  ------------------
Contributions:
Employer                                                                             1,509,073           1,314,067
Participants                                                                         1,722,006           1,535,647
Rollover                                                                                67,721           1,477,049
                                                                             ------------------  ------------------
                                                                                     3,298,800           4,326,763
                                                                             ------------------  ------------------
Assets transferred in from merged/terminated plans                                           -          13,670,154
                                                                             ------------------  ------------------
          Total additions                                                            4,466,754          19,405,155
                                                                             ------------------  ------------------
Deductions from net assets attributed to:
Net depreciation in fair value of investments                                       10,478,563             603,821
   Withdrawals and benefits paid to participants                                     4,321,767           3,905,463
    Administrative fees                                                                 15,311              10,139
                                                                             ------------------  ------------------
          Total deductions                                                          14,815,641           4,519,423
                                                                             ------------------  ------------------

    Net (decrease) increase in net assets available for benefits                   (10,348,887)         14,885,732

Net assets available for benefits at beginning of year                              42,586,327          27,700,595
                                                                             ------------------  ------------------
Net assets available for benefits at end of year                                   $32,237,440         $42,586,327
                                                                             ==================  ==================



See accompanying notes to financial statements.
                                       3




                           BERKSHIRE BANK 401(k) PLAN

                          NOTES TO FINANCIAL STATEMENTS

                     Years Ended December 31, 2008 and 2007


1.   DESCRIPTION OF THE PLAN

     The Berkshire  Bank 401(k) Plan (the "Plan") was  established  on April 11,
1993.

     The  following  brief  description  of the  Plan is  provided  for  general
     information purposes only.  Participants should refer to the Plan Agreement
     for a more complete description of the Plan's provisions.

     General

     The Plan is a defined  contribution plan covering all eligible employees of
     Berkshire Bank and  subsidiaries  (the "Bank" or the "Plan  Sponsor").  The
     Plan  is  subject  to the  provisions  of the  Employee  Retirement  Income
     Security Act of 1974 ("ERISA").  Vanguard Fiduciary Trust Company serves as
     the Trustee of the Plan. The Vanguard Group ("Vanguard" or the "Custodian")
     is the custodian of the Plan.

     In 2005,  the Plan Sponsor  terminated  its Employee  Stock  Ownership Plan
     ("ESOP").  During 2007,  active employees of the Bank were given the option
     to transfer  their  shares of stock from the ESOP into the Plan.  The value
     transferred  into the Plan is the  value of the  shares  as  posted  on the
     Nasdaq Stock Market as of the date of transfer.

     On November 1, 2006, Berkshire Bank acquired five local insurance agencies.
     These  insurance  agencies  all  participated  in one  plan,  the  Alliance
     Berkshire  Insurance 401(k) Plan  ("Alliance").  During 2007,  Alliance was
     merged  into the Plan.  Effective  on the merger  date,  all  employees  of
     Alliance  followed the eligibility  requirements of the Plan but were given
     credit for hours of service with their previous employer.

     On September  21, 2007,  the Bank acquired  Factory Point  National Bank of
     Manchester  Center  ("Factory  Point").  Effective  November  5, 2007,  the
     Factory Point  National Bank 401(k) Profit Sharing Plan was merged into the
     Plan. Effective on the merger date, all employees of Factory Point followed
     the eligibility requirements of the Plan but were given credit for hours of
     service with their previous employer.


                                       4



                           BERKSHIRE BANK 401(k) PLAN

                    NOTES TO FINANCIAL STATEMENTS (Continued)


     DESCRIPTION OF THE PLAN (continued)

     Contributions

     Each  year,   participants  may  contribute  a  percent  of  pretax  annual
     compensation,  excluding certain types of restricted compensation,  subject
     to certain limitations as defined by the Plan and the Internal Revenue Code
     ("IRC").  The maximum  participant  deferral was $15,500 for the Plan years
     ended  December  31, 2008 and 2007.  In  addition,  all  employees  who are
     eligible to make salary reductions under the Plan and who have attained age
     50  before  the  close  of the  Plan  year are  eligible  to make  catch-up
     contributions,   as  defined  by  the   Economic   Growth  and  Tax  Relief
     Reconciliation  Act of 2001  ("EGTRRA").  Participants  may also contribute
     rollover amounts representing distributions from other qualified retirement
     plans and IRAs.  Participants  direct the investment of their contributions
     into  various  investment  options  offered by the Plan.  Participants  may
     change their rate of contribution each pay period.

     The Bank matches a portion of eligible employee contributions.  During 2008
     and 2007, the Bank matched 100% of eligible employee contributions up to 4%
     of the participant's annual compensation.

     In addition, the Bank makes a Safe Harbor non-elective  contribution to the
     account  of  each  eligible  employee  in an  amount  equal  to  3% of  the
     participant's  annual  compensation,  excluding certain types of restricted
     compensation.

     Plan Eligibility

     Employees  of the Bank  are  eligible  to  participate  in the  Plan  after
     attaining  twenty-one  years of age and completing one year of service with
     1,000 hours during their initial year of  employment.  500 hours of service
     must be  exceeded  each  subsequent  year to avoid a break  in  eligibility
     service.  Service  credit  is given to  employees  of  certain  predecessor
     employers as described in the Plan document for  participation  and vesting
     purposes.  Employees may join the Plan on the first of the month  following
     the month in which eligibility requirements are satisfied.

     Participant Accounts

     Each participant's account is credited with the participant's
        contribution and allocations of (a) the Company's matching and
        additional contributions for non-highly compensated employees, if any,
        and (b) the Plan's investment earnings. Allocations are based on
        participant earnings or account balances, as defined by the Plan. The
        benefit to which a participant is entitled is the benefit that can be
        provided from the participant's vested account.

                                       5




                           BERKSHIRE BANK 401(k) PLAN

                    NOTES TO FINANCIAL STATEMENTS (Continued)


     DESCRIPTION OF THE PLAN (continued)

     Investments

     Participants  direct the investment of their  contributions into investment
     options offered by the Plan which include selected pooled separate accounts
     of Vanguard and common shares of Berkshire Hills Bancorp,  Inc., the parent
     company  of  the  Bank.   Employer   contributions  are  invested  in  each
     participant's  account according to the participant's  selected allocation.
     Participants  may change or transfer their  investment  options at any time
     via an automated telephone system or the Custodian's website.

     Vesting

     Participants  are 100% vested in all  contributions  plus  actual  earnings
     thereon.

     Participant Loans

     Participants may borrow from their fund accounts an amount equal to $50,000
     or 50% of their vested account balance, whichever is less. In addition, the
     $50,000  limit is reduced by the highest  outstanding  loan balance (of any
     previous loans made) in the previous  twelve months.  The loans are secured
     by the balance in the participant's  accounts and bear interest at The Wall
     Street  Journal  prime  rate  plus  one  percentage  point  as of the  loan
     application  review date.  Interest  rates ranged from 5.00% to 9.25% as of
     December 31, 2008. In general, principal and interest are paid ratably over
     a period not to exceed five years through regular payroll deductions. Loans
     used to finance the  participant's  principal  residence  are repaid over a
     period of time, up to 20 years.

     If a participant  fails to make a loan repayment by its due date, the total
     outstanding amount of the loan including any interest that has accrued will
     be defaulted and deemed a  distribution  to the  participant on the date of
     default.  Loan  defaults  were  $21,534  and  $14,263  for the years  ended
     December 31, 2008 and 2007, respectively.

     Payment of Benefits

     On termination of service due to death, disability,  normal retirement,  or
     attaining age 59 1/2 a participant  may elect to receive  either a lump sum
     amount  equal to the value of the  participant's  vested  interest in their
     account, annual installments,  or defer distribution until a later date. If
     the vested portion of a  participant's  account  balance is $1,000 or less,
     this  amount  is  paid as a lump  sum  distribution  as  soon  as  possible
     following  termination,  retirement,  disability,  or  to  the  beneficiary
     following death.

     Participants  may  request  a  benefit  payment  in the  case of  financial
     hardship, subject to certain limitations as defined by the Plan.






                           BERKSHIRE BANK 401(k) PLAN

                    NOTES TO FINANCIAL STATEMENTS (Continued)


     DESCRIPTION OF THE PLAN (concluded)

     Administrative Expenses

     The Plan's administrative  expenses are paid by either the Plan or the Plan
     Sponsor as provided by the Plan document.  Administrative  expenses paid by
     the Plan Sponsor were $16,130 and $15,050 for the years ended  December 31,
     2008 and 2007, respectively.

     Plan Termination

     Although it has not  expressed  any intent to do so, the Bank has the right
     under  the  Plan  to  discontinue  its  contributions  at any  time  and to
     terminate the Plan,  subject to the  provisions  of ERISA.  In the event of
     Plan  termination,  the net  assets  of the  Plan  would  be  allocated  as
     prescribed by ERISA and its related regulations.


2.      SUMMARY OF ACCOUNTING POLICIES

     A summary of significant  accounting policies  consistently  applied in the
     preparation of the accompanying financial statements follows.

     Basis of Accounting

     The accompanying  financial statements have been prepared using the accrual
     method of accounting.

     Use of Estimates

     In preparing financial statements in conformity with accounting  principles
     generally accepted in the United States of America,  management is required
     to make  estimates  and  assumptions  that affect the  reported  amounts of
     assets and liabilities, the disclosure of contingent assets and liabilities
     at the  date of the  financial  statements,  and the  reported  amounts  of
     revenues and expenses  during the reporting  period.  Actual  results could
     differ from those estimates.

     Investment Valuation and Income Recognition

     The Plan's  investments  are  stated at fair  value.  Shares of  registered
     investment companies are valued at quoted market prices which represent the
     net asset  value of shares  held by the Plan at  year-end.  Investments  in
     Berkshire Hills Bancorp, Inc. common stock and other equities are valued at
     the  closing  market  price as of the last  trade  date of the year.  Fixed
     income  securities are valued using the last quoted bid price.  Participant
     loans are valued at amortized cost, which approximates fair value.

                                       7




                           BERKSHIRE BANK 401(k) PLAN

                    NOTES TO FINANCIAL STATEMENTS (Continued)


     SUMMARY OF ACCOUNTING POLICIES (continued)

     Investment Valuation and Income Recognition (concluded)

     Purchases  and sales of  investments  are recorded on a  trade-date  basis.
     Investment  income is  recorded on the accrual  basis.  Dividend  income is
     recorded on the ex-dividend date.  Capital gain  distributions are included
     in dividend income.

     Effective  January  1,  2008,  the  Plan  adopted  Statement  of  Financial
     Accounting  Standards  No. 157, Fair Value  Measurements  ("SFAS No. 157"),
     issued by the Financial Accounting  Standards Board ("FASB").  SFAS No. 157
     defines  fair value as the price that would be received to sell an asset or
     paid to  transfer a  liability  in an orderly  transaction  between  market
     participants at the measurement  date and sets out a fair value  hierarchy.
     The fair value  hierarchy  gives the highest  priority to quoted  prices in
     active markets for identical assets or liabilities (Level 1) and the lowest
     priority to unobservable inputs (Level 3). Inputs are broadly defined under
     SFAS No. 157 as  assumptions  market  participants  would use in pricing an
     asset or liability. The three levels of the fair value hierarchy under SFAS
     No. 157 are described below:

     Level  1 -  Fair  values  designated  as  Level  1 are  valued  based  upon
     unadjusted  quoted  prices  in  active  markets  for  identical  assets  or
     liabilities  that the  reporting  entity  has the  ability to access at the
     measurement date.

     Level 2 - Fair values  designated  as Level 2 are valued  based upon quoted
     prices for similar assets and liabilities in active markets,  quoted prices
     for  identical or similar  assets and  liabilities  in markets that are not
     active,  and inputs other than quoted  prices that are  observable  for the
     asset or liability, either directly or by correlation or other means.

     Level 3 - Inputs for Level 3 fair values are  unobservable for the asset or
     liability  and include  situations  where there is little,  if any,  market
     activity  for the asset or  liability.  Such inputs are based upon the best
     information in the  circumstances  and may require  significant  management
     judgment or estimation.

     In certain cases, inputs used to measure fair value may fall into different
     levels of the fair value  hierarchy.  In such cases, an investment's  level
     within the fair value  hierarchy is based on the lowest level of input that
     is significant to the fair value measurement.  The Plan's assessment of the
     significance  of a particular  input to the fair value  measurement  in its
     entirety   requires   judgment  and  considers   factors  specific  to  the
     investment.


                                       8



                           BERKSHIRE BANK 401(k) PLAN

                    NOTES TO FINANCIAL STATEMENTS (Continued)


     SUMMARY OF ACCOUNTING POLICIES (concluded)

     Risks and Uncertainties

     The Plan invests in a variety of investment vehicles. Investment securities
     are exposed to various risks,  such as interest rate,  market,  and credit.
     Due to the level of risk associated with certain investment securities,  it
     is at least  reasonably  possible  that changes in the values of investment
     securities  will  occur  in the  near  term and  that  such  changes  could
     materially affect  participants'  account balances and the amounts reported
     in the statement of net assets available for benefits.

3.     CASH AND CASH EQUIVALENTS

     The following schedule presents the fair values of the Plan's cash and cash
     equivalents:

                                                        December 31,
                                         -------------------------------------
                                               2008                  2007
                                         ---------------       ---------------
Cash and cash equivalents:
* VGI Brokerage Option                      $ 129,711             $         -
* Vanguard Prime Money Market               4,204,262 (a)          3,385,352 (b)
                                         ---------------       ---------------
                                            4,333,973             $ 3,385,352
                                         ===============       ===============

(a)    Investment represents 5% or more of Plan net assets at December 31, 2008.
(b)    Investment represents 5% or more of Plan net assets at December 31, 2007.
       * Represents a party-in-interest under ERISA.

                                       9




                           BERKSHIRE BANK 401(k) PLAN

                    NOTES TO FINANCIAL STATEMENTS (Continued)


4.     INVESTMENTS, AT FAIR VALUE

     The following schedule presents the fair values of the Plan's investments:



                                                                   December 31,
                                                    -----------------------------------------
                                                          2008                    2007
                                                    ------------------      -----------------
Mutual funds:
                                                                           
* Royce Low Priced Stock                                  $ 341,569              $ 503,808
* Vanguard 500 Index Inv.                                 3,774,309 (a)          7,158,236 (b)
* Vanguard IT Treasury Inv.                               3,547,986 (a)          2,746,411 (b)
* Vanguard International Growth Fund                      1,802,055 (a)          3,506,924 (b)
* Vanguard Mid-Cap Index Fund                               795,103              1,713,087
* Vanguard Morgan Growth Inv.                               388,514                488,827
* Vanguard Selected Value                                   444,311                616,392
* Vanguard Small-Cap Growth Index                         1,184,596              2,081,181
* Vanguard TGT Retirement 2010                               67,076                      -
* Vanguard TGT Retirement 2015                            3,209,859 (a)          4,174,760 (b)
* Vanguard TGT Retirement 2020                              122,621                      -
* Vanguard TGT Retirement 2025                              814,461              1,274,355
* Vanguard TGT Retirement 2030                                1,791                      -
* Vanguard TGT Retirement 2035                              398,964                483,020
* Vanguard TGT Retirement 2040                               15,167                      -
* Vanguard TGT Retirement 2045                              481,538                602,980
* Vanguard TGT Retirement 2050                                3,024                      -
* Vanguard Target Retirement Inc.                         1,257,681              1,009,957
* Vanguard Total Stock Market Inv.                        3,404,548 (a)          5,647,432 (b)
* Vanguard Windsor II Fund Inv.                             744,732              1,095,670

Common stock:
* VGI Brokerage Option Company Stock                         82,365                 44,904
* Berkshire Hills Bancorp, Inc. Common Stock              4,481,745 (a)          5,197,438 (b)
                                                    ------------------      -----------------
                                                        $27,364,015            $38,345,382
                                                    ==================      =================


(a)   Investment represents 5% or more of Plan net assets at December 31, 2008.
(b)   Investment represents 5% or more of Plan net assets at December 31, 2007.
      * Represents a party-in-interest under ERISA.

                                       10


                           BERKSHIRE BANK 401(k) PLAN

                    NOTES TO FINANCIAL STATEMENTS (Continued)

     INVESTMENTS, AT FAIR VALUE (concluded)

     During 2008 and 2007, the Plan's investments (including investments bought,
     sold,  and held  during  the year)  appreciated  (depreciated)  in value as
     follows:

                                           December 31,
                                  ----------------------------------------
                                         2008                 2007
                                  -------------------   ------------------
Mutual funds                            $(11,227,509)           $ 429,995
Common stock                                 748,946           (1,033,816)
                                  -------------------   ------------------
                                        $(10,478,563)          $ (603,821)
                                  ===================   ==================

     The following table  summarizes the valuation of the Plan's  investments by
     the SFAS 157 fair value hierarchy levels as of December 31, 2008:



                                      Level 1              Level 2             Level 3             Fair Value
                                 -------------------   -----------------   -----------------   -------------------
                                                                                          
Cash and cash equivalents               $ 4,333,973           $       -           $ -              $ 4,333,973
Mutual funds                             22,799,905                   -             -               22,799,905
Common stock                              4,564,110                   -             -                4,564,110
Loans to participants                             -             539,452             -                  539,452
                                 -------------------   -----------------   -----------------   -------------------
               Total assets             $31,697,988           $ 539,452           $ -              $32,237,440
                                 ===================   =================   =================   ===================


5.     TAX STATUS

     The Bank adopted a Prototype  Plan whose most recent  determination  letter
     from the Internal Revenue Service,  dated August 22, 2001,  stated that the
     Plan and related Trust were designed in accordance with applicable sections
     of the IRC. The Plan has been amended since receiving this letter; however,
     the  Plan  Administrator   believes  the  Plan  is  currently  operated  in
     compliance with the applicable requirements of the IRC.

6.     ADMINISTRATION OF PLAN ASSETS

     The Plan assets are held by Vanguard  Fiduciary Trust Company,  the Trustee
     of the Plan.

     Bank  contributions,   participant  elective  deferrals,   and  participant
     accounts are held and  administered by Vanguard,  who invests cash received
     in accordance with  participants  instructions  and makes  distributions to
     participants.

     Certain administrative  functions are performed by officers or employees of
     the Bank.  No such  officers or  employees  receive  compensation  for such
     functions from the Plan.
                                       11




                           BERKSHIRE BANK 401(k) PLAN

                    NOTES TO FINANCIAL STATEMENTS (Concluded)


7.     RELATED PARTY TRANSACTIONS

     The Bank  contributed  $1,509,073  and $1,314,067 to the Plan for the years
     ended  December 31, 2008 and 2007,  of which $0 and $52,410 was owed to the
     Plan at December 31, 2008 and 2007,  respectively.  In  addition,  the Bank
     paid expenses in connection with the  administrations of the Plan, totaling
     $16,130  and  $15,050  for the  years  ended  December  31,  2008 and 2007,
     respectively.

     The Plan has investments in common stock of Berkshire Hills Bancorp,  Inc.,
     the parent  company of the Bank.  In  addition,  certain of the  investment
     options are managed by Vanguard.  Transactions in such investments  qualify
     as party-in-interest transactions.

8.     ASSETS TRANSFERRED IN FROM MERGED/TERMINATED PLANS

     The assets transferred in from merged plans during 2007 were as follows:

ESOP                                                            $ 1,943,781
Alliance                                                          2,650,583
Factory Point                                                     7,064,422
Adjustment to Berkshire Hills, Inc. common stock
    transferred in from cost value to market value                2,011,368
                                                          ------------------

                                                               $ 13,670,154
                                                          ==================
                                       12




                           BERKSHIRE BANK 401(k) PLAN

                    SCHEDULE H, LINE 4i - SCHEDULE OF ASSETS
                              (HELD AT END OF YEAR)

                                December 31, 2008




--------     -------------------------------------------------   -------------------------    ----------------
             Identity of Issuer, Borrower, Lessor or
             Similary Party and Description of                          Number                    Current
             Investment                                            of units/shares                value (1)
             -------------------------------------------------------------------------------------------------
                                                                                      
             Cash and cash equivalents:
   *          Vanguard Prime Money Market                             4,204,262.180            $ 4,204,262
   *          Vanguard Brokerage Option                                 129,711.080                129,711
             Mutual funds:
   *          Royce Low Priced Stock                                     37,289.169                341,569
   *          Vanguard 500 Index Inv.                                    45,424.348              3,774,309
   *          Vanguard IT Treasury Inv.                                 293,221.971              3,547,986
   *          Vanguard International Growth Fund                        147,709.457              1,802,055
   *          Vanguard Mid-Cap Index Fund                                67,381.597                795,103
   *          Vanguard Morgan Growth Inv.                                34,381.726                388,514
   *          Vanguard Selected Value                                    37,399.934                444,311
   *          Vanguard Small-Cap Growth Index                            99,545.922              1,184,596
   *          Vanguard TGT Retirement 2010                                3,808.951                 67,076
   *          Vanguard TGT Retirement 2015                              336,110.845              3,209,859
   *          Vanguard TGT Retirement 2020                                7,400.163                122,621
   *          Vanguard TGT Retirement 2025                               87,859.878                814,461
   *          Vanguard TGT Retirement 2030                                  115.238                  1,791
   *          Vanguard TGT Retirement 2035                               43,131.258                398,964
   *          Vanguard TGT Retirement 2040                                1,002.434                 15,167
   *          Vanguard TGT Retirement 2045                               50,317.448                481,538
   *          Vanguard TGT Retirement 2050                                  199.190                  3,024
   *          Vanguard Target Retirement Inc.                           132,109.394              1,257,681
   *          Vanguard Total Stock Market Inv.                          156,171.911              3,404,548
   *          Vanguard Windsor II Fund Inv.                              39,970.808                744,732
             Common Stock:
   *          VGI Brokerage Option Company Stock                         82,365.490                 82,365
   *          Berkshire Hills Bancorp, Inc. Common Stock                145,228.305              4,481,745
             Loan Fund:
              Participant loans                                        5.00% - 9.25%               539,452
                                                                                               -----------
                                                                                               $32,237,440
                                                                                               ===========

(1)  As allowed  by ERISA,  cost  information  may be  omitted  with  respect to
     participant or beneficiary directed investments under an individual account
     plan.

*    Represents a party-in-interest as defined by ERISA.

See report of independent registered public accounting firm.

                                       13



                                   SIGNATURES


     The Plan.  Pursuant to the  requirements of the Securities  Exchange Act of
1934, the trustees (or other persons who  administer the employee  benefit plan)
have  duly  caused  this  annual  report  to be  signed  on  its  behalf  by the
undersigned hereunto duly authorized.


                                            BERKSHIRE BANK 401(k) PLAN






Date June 25, 2009                By:      /s/ Linda A. Johnston
                                           ------------------------------------
                                  Name:    Linda A. Johnston
                                  Title:   Senior Vice President Human Resources
                                           Berkshire Bank





            Consent of Independent Registered Public Accounting Firm




We consent to the  incorporation by reference in the  Registration  Statement of
Berkshire  Hills  Bancorp,  Inc.  on Form S-8 (SEC File No.  333-146604)  of our
report dated June 24, 2009,  appearing in this Annual Report on Form 11-K of the
Berkshire Bank 401(k) Plan for the year ended December 31, 2008.



/s/ Wolf & Company, P.C.
Wolf & Company, P.C.
Boston, Massachusetts
June 24, 2009