1


                            SCHEDULE 14A INFORMATION
PROXY STATEMENT PURSUANT TO SECTION 14(A) OF THE SECURITIES EXCHANGE ACT OF 1934

Filed by the registrant |X|
Filed by a party other than the registrant |_|


Check the appropriate box:
| |  Preliminary proxy statement
|_|  Confidential, for Use of the Commission only (as permitted by Rule 14a-6(e)
     (2))
|_|  Definitive proxy statement
|X|  Definitive additional materials
|_|  Soliciting material pursuant to Rule 14a-12


                          Berkshire Hills Bancorp, Inc.
- --------------------------------------------------------------------------------
                (Name of Registrant as Specified in Its Charter)


- --------------------------------------------------------------------------------
    (Name of Person(s) Filing Proxy Statement, if other than the Registrant)

Payment of filing fee (Check the appropriate box):
|X|  No fee required.
|_|  Fee computed on table below per Exchange Act Rules 14a-6(i)(1) and 0-11.

(1)  Title of each class of securities to which transaction applies:
               N/A
- --------------------------------------------------------------------------------
(2)  Aggregate number of securities to which  transactions  applies:
               N/A
- --------------------------------------------------------------------------------
(3)  Per unit price or other underlying valueof transaction computed pursuant to
     Exchange  Act Rule 0-11 (set  forth the  amount on which the  filing fee is
     calculated and state how it was determined:
               N/A
- --------------------------------------------------------------------------------
(4)  Proposed maximum aggregate value of transaction:
               N/A
- --------------------------------------------------------------------------------
(5)  Total fee paid:
               N/A
- --------------------------------------------------------------------------------
|_|  Fee paid previously  with  preliminary  materials.
|_|  Check box if any part of the fee is offset as provided by Exchange Act Rule
     0-11(a)(2)  and identify the filing for which the  offsetting  fee was paid
     previously.  Identify the previous filing by registration statement number,
     or the Form or Schedule and the date of its filing.

(1)  Amount Previously Paid:
               N/A
- --------------------------------------------------------------------------------
(2)  Form, Schedule or Registration Statement No.:
               N/A
- --------------------------------------------------------------------------------
(3)   Filing Party:
               N/A
- --------------------------------------------------------------------------------
(4)   Date Filed:
               N/A
- --------------------------------------------------------------------------------


 2


                            Berkshire Bank Letterhead

Dear ESOP Participant:

      On behalf of the Board of Directors, I am forwarding you the attached vote
authorization  form for the purpose of  conveying  your voting  instructions  to
Eastern Bank and Trust Company (the "ESOP  Trustee") on the proposals  presented
at the Annual Meeting of  Stockholders  of Berkshire  Hills  Bancorp,  Inc. (the
"Company") on May 3, 2001. Also enclosed is a Notice and Proxy Statement for the
Company's Annual Meeting of Stockholders  and the Berkshire Hills Bancorp,  Inc.
Annual Report to Stockholders.

      As a participant in the Berkshire Bank Employee Stock  Ownership Plan (the
"ESOP"),  you are entitled to vote all shares of Company common stock  allocated
to your account as of March 15, 2001.  These allocated  shares of Company common
stock will be voted as directed by you;  provided your instructions are received
by the ESOP  Trustee  by  April  23,  2001.  The ESOP  Trustee,  subject  to its
fiduciary duties,  will vote any unallocated  shares of Company common stock and
any allocated  shares of Company common stock for which timely  instructions are
not provided in a manner calculated to most accurately  reflect the instructions
from  participants  regarding  the shares of Company  common stock  allocated to
participants' accounts.

      At this  time,  in order to direct  the  voting of the  shares of  Company
common  stock  allocated  to your ESOP  account,  please  complete  and sign the
attached  vote  authorization  form and return it in the  enclosed  postage-paid
envelope.  The ESOP Trustee must  receive your  instructions  by April 23, 2001.
Your vote will not be revealed, directly or indirectly, to any officer, employee
or director of the Company or Berkshire  Bank.  The votes will be tallied by the
ESOP Trustee and the ESOP Trustee will use the voting  instructions  it receives
to vote the shares of Company common stock in the ESOP Trust.

                                          Sincerely,

                                          /s/ James A. Cunningham, Jr.

                                          James A. Cunningham, Jr.
                                          President and Chief Executive Officer





 3



Name:____________________
Shares:____________________


                             VOTE AUTHORIZATION FORM

      I, the  undersigned,  understand that Eastern Bank and Trust Company,  the
ESOP  Trustee,  is the holder of record and custodian of all shares of Berkshire
Hills  Bancorp,  Inc.  (the  "Company")  common stock under the  Berkshire  Bank
Employee Stock  Ownership  Plan. I understand  that my voting  instructions  are
solicited on behalf of the Company's  Board of Directors for the Annual  Meeting
of Stockholders to be held on May 3, 2001.

      You are to vote my shares as follows:

1.    The  election as directors  of all  nominees  listed  (unless the "For All
      Except" box is marked and the instructions below are complied with).

            Henry D. Granger, Edward G. McCormick, Raymond B. Murray, III,
            Robert A. Wells, Ann H. Trabulsi and Anne Everest Wojtkowski

                                                            FOR ALL
            FOR               VOTE WITHHELD                 EXCEPT
            ---               -------------                 ------

            |_|                   |_|                        |_|

INSTRUCTION:  To withhold your vote for any  individual  nominee,  mark "FOR ALL
EXCEPT" and write that nominee's name on the line provided below.


================================================================================

      2.    The  ratification  of  the  appointment  of  Wolf & Company, P.C. as
            independent auditors of Berkshire Hills Bancorp, Inc. for the fiscal
            year ending December 31, 2001.

            FOR                     AGAINST                 ABSTAIN
            ---                     -------                 -------

            |_|                       |_|                     |_|


THE BOARD OF DIRECTORS RECOMMENDS A VOTE "FOR" THE LISTED PROPOSALS.

      The ESOP Trustee is hereby  authorized to vote the shares  attributable to
me in its trust capacity as indicated above.


- ---------------------------------           ------------------------------------
            Date                                      Signature

PLEASE DATE, SIGN AND RETURN THIS FORM IN THE ENCLOSED  POSTAGE-PAID ENVELOPE NO
LATER THAN APRIL 23, 2001.




 4



                          BERKSHIRE HILLS BANCORP, INC.
                                   LETTERHEAD


Dear Stock Award Recipient:

      On behalf of the Board of Directors, I am forwarding you the attached vote
authorization  form for the purpose of  conveying  your voting  instructions  to
First  Bankers  Trust Company (the  "Incentive  Plan  Trustee") on the proposals
presented at the Annual Meeting of Stockholders of Berkshire Hills Bancorp, Inc.
(the  "Company") on May 3, 2001.  Also enclosed is a Notice and Proxy  Statement
for the  Company's  Annual  Meeting  of  Stockholders  and the  Berkshire  Hills
Bancorp, Inc. Annual Report to Stockholders.

      As a participant  in the Berkshire  Hills Bancorp,  Inc. 2000  Stock-Based
Incentive Plan (the  "Incentive  Plan"),  you are entitled to vote all shares of
restricted  stock awarded to you under the Incentive  Plan as of March 15, 2001.
The  Incentive  Plan Trustee will vote those shares of the Company  common stock
held in the Incentive  Plan Trust in accordance  with  instructions  it receives
from you and the other stock award recipients.

      At this  time,  in order to direct  the  voting of  Company  common  stock
awarded to you under the Incentive Plan, you must complete and sign the attached
vote authorization form and return it in the enclosed  postage-paid  envelope by
April 23, 2001.  The votes will be tallied by the Incentive Plan Trustee and the
Incentive Plan Trustee will use the voting  instructions it receives to vote the
shares of Company common stock held in the Incentive Plan Trust.

                                          Sincerely,

                                          /s/ James A. Cunningham, Jr.

                                          James A. Cunningham, Jr.
                                          President and Chief Executive Officer








 5


Name:____________________
Shares:____________________


                             VOTE AUTHORIZATION FORM
                             -----------------------

      I, the  undersigned,  understand  that First  Bankers Trust  Company,  the
Incentive  Plan Trustee,  is the holder of record and custodian of all shares of
Berkshire Hills Bancorp,  Inc. (the "Company")  common stock under the Berkshire
Hills Bancorp, Inc. 2000 Stock-Based Incentive Plan. I understand that my voting
instructions are solicited on behalf of the Company's Board of Directors for the
Annual Meeting of Stockholders to be held on May 3, 2001.

      You are to vote my shares as follows:

1.    The  election as directors  of all  nominees  listed  (unless the "For All
      Except" box is marked and the instructions below are complied with).

            Henry D. Granger, Edward G. McCormick, Raymond B. Murray, III,
            Robert A. Wells, Ann H. Trabulsi and Anne Everest Wojtkowski

                                                            FOR ALL
            FOR               VOTE WITHHELD                 EXCEPT
            ---               -------------                 ------

            |_|                   |_|                        |_|

INSTRUCTION:  To withhold your vote for any  individual  nominee,  mark "FOR ALL
EXCEPT" and write that nominee's name on the line provided below.


================================================================================

      2.    The  ratification  of  the  appointment  of  Wolf & Company, P.C. as
            independent auditors of Berkshire Hills Bancorp, Inc. for the fiscal
            year ending December 31, 2001.

            FOR                     AGAINST                 ABSTAIN
            ---                     -------                 -------

            |_|                       |_|                     |_|


THE BOARD OF DIRECTORS RECOMMENDS A VOTE "FOR" THE LISTED PROPOSALS.

      The  Incentive  Plan  Trustee  is  hereby  authorized  to vote the  shares
attributable to me in its trust capacity as indicated above.


- --------------------------------           -------------------------------------
            Date                                      Signature

PLEASE DATE, SIGN AND RETURN THIS FORM IN THE ENCLOSED  POSTAGE-PAID ENVELOPE NO
LATER THAN APRIL 23, 2001.