Document:

SUPPLEMENTAL EXECUTIVE RETIREMENT PLAN
                                     FOR THE
                    CHIEF EXECUTIVE OFFICER OF BERKSHIRE BANK

                                    Article 1
                      Description, Purpose and Definitions

     1.1 Name. The name of this Plan is the "Berkshire Bank Supplemental
Executive Retirement Plan."

     1.2 Purpose. The purpose of the Plan is to promote the retention of Michael
P. Daly, the Chief Executive Officer of the Company, by providing an additional
source of retirement income to supplement that available to him from other
sources.

     1.3 Definitions. For purposes of the Plan, the following words and phrases
shall have the meanings indicated, unless the context clearly indicates
otherwise.

     "Bank" means Berkshire Bank, Pittsfield, Massachusetts.

     "Cause" means termination of employment because of Executive's personal
dishonesty, willful misconduct, breach of fiduciary duty involving personal
profit, intentional failure to perform stated duties, willful violation of any
law, rule or regulation (other than traffic violations or similar infractions)
or a final cease-and-desist order.

     "Change in Control" means an event of a nature that: (i) would be required
to be reported in response to Item 1(a) of the current report on Form 8-K, as in
effect on the date hereof, pursuant to Section 13 or 15(d) of the Securities
Exchange Act of 1934 (the "Exchange Act"); or (ii) results in a Change in
Control of the Bank or the Company within the meaning of the Bank Change in
Control Act and the Rules and Regulations promulgated by the Federal Deposit
Insurance Corporation ("FDIC") at 12 C.F.R. ss. 303.4(a) with respect to the
Bank and the Board of Governors of the Federal Reserve System ("FRB") at 12
C.F.R. ss. 225.41(b) with respect to the Company, as in effect on the date
hereof; or (iii) results in a transaction requiring prior FRB approval under the
Bank Holding Company Act of 1956 and the regulations promulgated thereunder by
the FRB at 12 C.F.R. ss. 225.11, as in effect on the date hereof except for the
Company's acquisition of the Bank; or (iv) without limitation such a Change in
Control shall be deemed to have occurred at such time as (A) any "person" (as
the term is used in Sections 13(d) and 14(d) of the Exchange Act) is or becomes
the "beneficial owner" (as defined in Rule 13d-3 under the Exchange Act),
directly or indirectly, of securities of the Bank or the Company representing
20% or more of the Bank's or the Company's outstanding securities except for any
securities of the Bank purchased by the Company in connection with the
conversion of the Bank to the stock form and any securities purchased by any
tax-qualified employee benefit plan of the Bank; or (B) individuals who
constitute the Board of Directors on the date hereof (the "Incumbent Board")
cease for any reason to constitute at least a majority thereof, provided that
any person becoming a director subsequent to the date hereof whose election was

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approved by a vote of at least three-quarters (3/4) of the directors comprising
the Incumbent Board, or whose nomination for election by the Company's
stockholders was approved by the same Nominating Committee serving under an
Incumbent Board, shall be, for purposes of this clause (B), considered as though
he were a member of the Incumbent Board; or (C) a plan of reorganization,
merger, consolidation, sale of all or substantially all the assets of the Bank
or the Company or similar transaction occurs in which the Bank or Company is not
the resulting entity; or (D) solicitations of shareholders of the Company, by
someone other than the current management of the Company, seeking stockholder
approval of a plan of reorganization, merger or consolidation of the Company or
Bank or similar transaction with one or more corporations as a result of which
the outstanding shares of the class of securities then subject to the plan or
transaction are exchanged for or converted into cash or property or securities
not issued by the Bank or the Company shall be distributed; or (E) a tender
offer is made for 20% or more of the voting securities of the Bank or the
Company.

     "Company" means Berkshire Hills Bancorp, Inc., a Delaware corporation.

     "Disability" means Executive suffers a sickness, accident or injury which
has been determined by the carrier of any individual or group disability
insurance policy covering Executive, or by the Social Security Administration,
to be a disability rendering Executive totally and permanently disabled.
Executive must submit proof to the Bank of the carrier's or Social Security
Administration's determination at the request of the Bank.

     "Executive" means Michael P. Daly, Chief Executive Officer of the Bank.

     "Final Average Earnings" means the highest average of the total salary and
bonus paid to executive for any three consecutive completed calendar years
preceding termination.

     "Social Security Benefit" means the amount, as determined by the
Administrator in its discretion and based upon Executive's estimated earnings
history to the date of his termination of employment with the Bank, to which he
will be entitled under the old age provisions of the Social Security Act upon
attainment of the normal Social Security retirement age (assuming no changes in
compensation between the time of Executive's termination from employment and his
normal retirement age for purposes of receiving his receiving his Social
Security Benefit).

                                    Article 2
                                   Eligibility

     2.1 Entitlement to Benefits. Except to the extent provided in Sections 3.3,
3.4 and 3.5, Executive shall become entitled to receive a benefit under the Plan
only if his employment with the Bank terminates for reasons other than Cause
after he has attained age 62. Notwithstanding anything in this Plan to the
contrary, no benefit shall be payable to Executive if his employment is
terminated for Cause.

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                                    Article 3
                        Supplemental Retirement Benefits

     3.1 Basic Benefit. Subject to the succeeding provisions of this Article,
Executive shall be entitled to an annual benefit equal to 70% of his Final
Average Earnings upon his termination of employment (other than for Cause) at or
after attaining age 62.

     3.2 Other Retirement Income Reduction.

          A.   Executive's annual benefit determined under Section 3.1 shall be
               reduced by the sum of the following amounts:

               (1)  50% of the amount of his annual Social Security Benefit;

               (2)  The amount of his annual benefit under the Pension Plan; and

               (3)  The value of his annual benefit attributable to employer
                    matching and non-elective contributions made by the Bank to
                    the Bank's 401(k) Plan and his employer contributions under
                    the Berkshire Bank Employee Stock Ownership Plan.

          B.   If any benefit described in Subsection A is not payable as a
               single life annuity or does not commence at the same time as
               Executive's benefit under this Plan, the Administrator shall, for
               purposes of this section, convert the value of such benefit into
               an actuarially equivalent single life annuity benefit commencing
               at the same time as the benefit under this Plan.

          C.   If Executive would be entitled to a benefit described in
               Subsection A but for his failure to apply for such benefit,
               Subsection A will be applied as if he had applied for and
               received the benefit.

          D.   Changes in a benefit described in Subsection A that occur after
               commencement of Executive's benefit under this Plan because of
               changes in the plan or program under which the benefit is
               provided or because of cost of living adjustments will not change
               the amount of the reduction under Subsection A.

     3.3  Early Retirement Benefit. If Executive's termination of employment
          occurs prior to the date he attains age 62 but after attaining age 55,
          other than by reason of his death or Disability or following a Change
          in Control, he shall be entitled to a percentage of the basic benefit
          determined under Sections 3.1 and 3.2. The percentage of Executive's
          benefit under this Section 3.3 shall be determined as follows:

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<PAGE>

               (i)  If he retires during the calendar year in which he attains
                    age 55, the benefit otherwise determined under Sections 3.1
                    and 3.2 shall be reduced by 50%.

               (ii) If he retires during the calendar year in which he attains
                    age 56, the benefit otherwise determined under Sections 3.1
                    and 3.2 shall be reduced by 40%.

               (iii) If he retires during the calendar year in which he attains
                    age 57, the benefit otherwise determined under Sections 3.1
                    and 3.2 shall be reduced by 30%.

               (iv) If he retires during the calendar year in which he attains
                    age 58, the benefit otherwise determined under Sections 3.1
                    and 3.2 shall be reduced by 20%.

               (v)  If he retires during the calendar year in which he attains
                    age 59, the benefit otherwise determined under Sections 3.1
                    and 3.2 shall be reduced by 15%.

               (vi) If he retires during the calendar year in which he attains
                    age 60, the benefit otherwise determined under Sections 3.1
                    and 3.2 shall be reduced by 10%.

               (vii) If he retires during the calendar year in which he attains
                    age 61, the benefit otherwise determined under Sections 3.1
                    and 3.2 shall be reduced by 5%.

     Such benefit shall be paid in accordance with Executive's election under
Section 3.6 at the time specified in Section 3.7.

     3.4  Death and Disability Benefits.

          A.   If Executive dies while employed by the Bank or terminates
               employment by reason of his Disability, there shall be paid to
               his or his designated beneficiary an amount equal to the benefit
               he would have received under Sections 3.1 and 3.2 if he had
               retired on the date immediately preceding his date of death or
               termination of employment and, as of such date, was deemed to
               satisfy the age requirement of Section 3.1. Such benefit shall be
               paid in accordance with his election under Section 3.6 at the
               time specified in Section 3.7.

          B.   If Executive dies after his entitlement to a benefit has been
               established by reason of his termination of employment but prior
               to the time that benefit payment(s) have commenced, such
               payment(s) shall be made to his beneficiary in accordance with
               his election.

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<PAGE>

          C.   Executive may, on a form prescribed by and filed with the
               Administrator, designate a beneficiary to receive any death
               benefit payable under this section. If no effective beneficiary
               designation is on file at the time of his death, the death
               benefit under this section shall be paid as follows:

               (1)  To his surviving spouse; or

               (2)  If no spouse survives, to his surviving children in equal
                    shares, with the descendants of a child who has predeceased
                    him taking such child's share by representation; or

               (3)  If none of his spouse and descendants is living, to the
                    representative of his estate.

          D.   The automatic beneficiaries set forth in Subsection C and, except
               as otherwise provided in Executive's duly filed beneficiary
               designation, the beneficiaries named in such designation, shall
               become fixed at his death so that if a beneficiary survives him
               but dies before final payment of the death benefit, any remaining
               death benefits shall be paid to the representative of such
               beneficiary's estate.

     3.5  Change in Control Benefit

     If Executive terminates employment with the Bank following a Change in
Control (other than for Cause), there shall be paid to him an amount equal to
the benefit he would have received if he had retired on the date immediately
preceding his date of termination of employment and, as of such date, was deemed
to satisfy the age requirements of Section 3.1. Such benefit shall be paid in
accordance with his election under Section 3.6 at the time specified in Section
3.7. The benefit payable under this provision shall be calculated using
Executive's Final Average Earnings as of his date of termination.

     3.6  Form of Benefit.

          A.   Upon Executive's entitlement to a benefit under this Plan, his
               benefit shall be paid in the form of (i) a single life annuity
               with 10 annual payments guaranteed or (ii) a lump sum which is
               actuarially equivalent to the annuity form of payment in (i), as
               designated by Executive on an election form designated by the
               Bank for such purpose.

          B.   Executive may, while employed by the Bank, change the form in
               which his benefits shall be paid by filing a revised election
               indicating such change at least one (1) calendar year prior to
               the date payments are to commence. Such election shall be
               irrevocable beginning one (1) calendar year prior to the date
               payments are to commence. No changes in the form

                                       5
<PAGE>

               of benefit payment shall be permitted following his termination
               of employment.

     3.7  Time of Payment/Calculation of Lump Sum.

          A.   Benefit payments made to Executive or Executive's beneficiary
               pursuant to Sections 3.1 or 3.4 shall commence in accordance with
               his election under Section 3.6 not later than 60 days following
               the his termination of employment.

          B.   Benefit payments made to Executive or Executive's beneficiary
               pursuant to Sections 3.3 or 3.5 shall commence in accordance with
               his election under Section 3.6 not later than 60 days following
               the date he attains age 62. Notwithstanding the foregoing, with
               respect to a benefit payable pursuant to Section 3.5, Executive
               may, with the consent of the Bank, elect to receive the lump sum
               equivalent of the benefit that would have otherwise been paid
               commencing not later than 60 days following the date he attains
               age 62. If Executive makes such an election, and the Bank
               consents, then the lump sum equivalent will be paid no later than
               the date on which the Change in Control occurs.

          C.   For purposes of this Plan, any lump sum calculation shall be made
               assuming a mortality age using the 1994 Group Annuity Reserve
               (GRA) table and a discount rate of  six percent (6%).

     3.8 Payment in the Event of Incapacity or Minority. If the Administrator,
in its discretion, determines that any person entitled to receive any payment
under this Plan is physically, mentally or legally incapable of receiving or
acknowledging receipt of payment, and no legal representative has been appointed
for such person, the Administrator in its discretion may (but shall not be
required to) cause any sum otherwise payable to such person to be paid to one or
more legal person(s) as may be chosen by the Administrator from among the
following: the institution maintaining such person, such person's spouse,
children, parents or other relatives by blood or marriage, a custodian under any
applicable Uniform Transfers to Minors Act or any other person determined by the
Administrator to have incurred expense for such person. The Administrator's
payment, based upon its good faith determination of the incapacity of the person
otherwise entitled to payments under this Plan and the existence of any other
person specified above, shall be conclusive and binding on all persons. Any such
payment shall be a complete discharge of the liabilities of the Company under
this Plan to the extent of such payment.

                                    Article 4
                               Source of Benefits

     4.1 Employer Funds. This Plan is unfunded, and all benefits payable to
Executive and his beneficiaries shall be payable solely from the general assets
of the Bank. Executive shall be required or permitted to make any contribution
to the Plan.

                                       6
<PAGE>

     4.2 Trust Fund. The Bank may establish a trust from which part or all of
the benefits under the Plan are to be paid. If a trust is established, all of
the principal and income of such trust shall remain subject to the claims of the
Bank's creditors until applied to the payment of benefits.

     4.3 Executive's Right to Funds. This Plan constitutes a mere promise by the
Bank to make benefit payments in the future. Beneficial ownership of any assets,
whether cash or investments, that the Bank may earmark or place in trust to pay
Executive's benefits under this Plan shall at all times remain in the Bank, and
neither Executive nor his beneficiaries shall have any property interest in any
specific assets of the Bank. To the extent Executive or any other person
acquires a right to receive payments from the Bank under this Plan, such right
shall be no greater than the right of any unsecured general creditor of the
Bank.

                                    Article 5
                                 Administration

     5.1 Administrator. The Board of Directors of the Bank shall be the
Administrator of the Plan. The Board may delegate any of its administrative
functions to another person, subject to the revocation of such delegation at any
time.

     5.2 Discretion. The Administrator shall also have the discretionary power
and authority, which it shall exercise in good faith, to determine whether
Executive is entitled to a benefit under the Plan, the identity of Executive's
beneficiaries, and the amount and form of the benefit payable to Executive or
his beneficiary. The Administrator shall have the discretion and authority to
interpret the Plan and to make such rules and regulations as it deems necessary
for the administration of the Plan and to carry out its purposes. The
determinations of the Administrator shall be conclusive and binding on all
persons.

     5.3 Determination of Benefit. The Administrator's good faith determination
of the benefits to which Executive or his beneficiaries are entitled under this
Plan shall be conclusive and binding on all persons; provided, however, that
this provision shall not preclude the Administrator's correcting any error the
Administrator determines to have been made in the computation of any benefit.
The Administrator shall be entitled to recover from any Participant or
beneficiary, or from his estate, the amount of any overpayment of benefits and
may reduce the amount of future benefits payable to any individual by the amount
of any overpayment made with respect to Executive.

     5.4 Benefit Claim Procedure. Within a reasonable period of time following
Executive's termination of employment, the Administrator will inform Executive
or his beneficiary of the amount of benefits, if any, payable from the Plan. Not
later than 30 days after receipt of such notification, Executive or his
beneficiary may file with the Administrator a written claim objecting to the
amount of benefits payable under the Plan. The Administrator, not later than 90
days after receipt of such claim, will render a written decision to the claimant
on the claim. If the claim is denied, in whole or in part, such decision will
include the reason or reasons for the denial, a reference to the Plan provision
that is the basis for the denial, a description of additional material or
information, if any, necessary for the claimant to perfect the claim, an

                                       7
<PAGE>

explanation as to why such information or material is necessary and an
explanation of the Plan's claim procedure. The claimant may file with the
Administrator, not later than 60 days after receiving the Administrator's
written decision, a written notice of request for review of the decision, and
the claimant or the claimant's representative may review Plan documents which
relate to the claim and may submit written comments to the Administrator. Not
later than 60 days after receipt of such review request, the Administrator will
render a written decision on the claim, which decision will include the specific
reasons for the decision, including a reference to the Plan's specific
provisions where appropriate. The foregoing 90- and 60-day periods during which
the Administrator must respond to the claimant may be extended by up to an
additional 90 or 60 days, respectively, if special circumstances beyond the
Administrator's control so require.

     5.5 Indemnification. The Bank shall indemnify the Administrator and each
other person to whom administrative functions are delegated against any and all
liabilities that may arise out of their administration of the Plan, except those
that are imposed on account of such person's willful misconduct.

     5.6 Limitation of Authority. No person performing any administrative
functions with respect to the Plan shall exercise, or participate in the
exercise of, any discretion with respect to his own benefit under the Plan. This
provision shall not preclude such person from exercising discretionary authority
with respect to the generally applicable provisions of the Plan, even though
such person's benefit may be affected by such exercise.

                                    Article 6
                                  Miscellaneous

     6.1 Actuarial Equivalency. Except as otherwise provided for in Section
3.7C, whenever an actuarial equivalent must be determined under this Plan, it
sshall be determined using reasonable actuarial factors elected by the
Administrator.

     6.2 Termination of Employment. Executive shall be deemed to have terminated
employment for purposes of this Plan when he or she has ceased to provide
service to the Bank as an employee.

     6.3 Effective Date. This Plan is effective as of December 1, 2003.

     6.4 No Employment Rights. Nothing contained in this Plan shall be construed
as conferring upon Executive the right to continue in the employ of the Bank.

     6.5 No Compensation Guarantees. Nothing contained in this Plan shall be
construed as conferring upon Executive the right to receive any specific level
of compensation; nor shall the Bank be prevented in any way from modifying the
manner or form in which Executive is to be compensated.

     6.6 Effect on Benefit Plans. Neither benefits accrued by Executive under
this Plan nor amounts paid pursuant to the Plan following his termination of
employment shall be deemed to be salary or other compensation to him for the
purpose of computing benefits to which he

                                       8
<PAGE>

may be entitled under any pension plan or other employee benefit plan or
arrangement sponsored by the Bank, except to the extent such other plan
expressly provides otherwise.

     6.7  Rights and Benefits Not Assignable. The rights and benefits of
Executive and any other person or persons to whom payments may be made pursuant
to this Plan are personal and, except for payments made to the representative of
a person's estate which may be assigned to the persons entitled to such estate,
shall not be subject to any voluntary or involuntary anticipation, alienation,
sale, assignment, pledge, transfer, encumbrance, attachment, garnishment by
creditors of Executive or such person or other disposition.

     6.8  Amendment and Termination.

          A.   The Board of Directors of the Bank may amend this Plan in such
               manner as it deems advisable, provided that no amendment shall
               reduce the accrued benefit of Executive, determined as of the
               date of the adoption of such amendment.

          B.   The Bank may terminate this Plan at any time. No person shall
               accrue any additional benefits under the Plan following the date
               of its termination. However, the termination of the Plan shall
               not affect Executive's right to receive payment of his accrued
               benefit (determined as of the date of the Plan's termination)
               upon termination of employment; provided Executive would have
               been entitled to a benefit upon termination of employment if the
               Plan had not been terminated.

     6.9 Governing Law. Except to the extent preempted by federal law, this Plan
shall be construed in accordance with, and governed by, the laws of the
Commonwealth of Massachusetts without regard to rules relating to choice of law.

     6.10 Entire Agreement. This Plan constitutes the entire understanding
between the Bank and each Participant as to the subject matter hereof. No rights
are granted to Executive by virtue of this Agreement other than those
specifically set forth herein.

                                       9Exhibit 10.16

                                    AGREEMENT

      THIS AGREEMENT is dated as of December 4, 2003, and is by and between
Robert A. Wells (herein "Mr. Wells") of Lenox, Massachusetts, and Berkshire
Hills Bancorp, Inc. (the "Holding Company") and Berkshire Bank ("Berkshire
Bank") (collectively "Berkshire") with a principal place of business in
Pittsfield, Massachusetts.

      WHEREAS, Mr. Wells' employment by Berkshire and his engagement as an
independent contractor by the Berkshire Hills Foundation and Greater Berkshire
Foundation, Inc. (collectively the "Foundations") shall terminate, effective
December 19, 2003 (the "Retirement Date");

      WHEREAS, Mr. Wells and Berkshire entered into an agreement regarding the
terms and conditions of his separation from Berkshire and the Foundations, a
copy of which is attached hereto as Exhibit A (the "Retirement Agreement").

      NOW, THEREFORE, in consideration of the foregoing and of the agreements
hereinafter set forth, the parties hereto mutually agree as follows:

      1. Mr. Wells hereby elects that his retirement date shall be December 19,
2003. On or before December 26, 2003, the Bank will pay to Mr. Wells the
$200,000.00 lump sum payment as provided in the Retirement Agreement and Mr.
Wells will refund to Berkshire the sum of $20,500.00 for the Royal Macabees (now
Reassure America) Policy premium payments made by Berkshire on his behalf. Upon
receipt of that $20,500.00, Berkshire acknowledges that all such amounts are
paid in full by Mr. Wells. Berkshire and Mr. Wells will fulfill all of their
respective obligations under the Retirement Agreement notwithstanding the
reciprocal releases set forth below.

      2. In consideration of the foregoing, Mr. Wells, for himself, his heirs,
administrators, executors and assigns, with full understanding of the content
and legal effect of this Release, hereby releases, discharges and covenants not
to sue Berkshire or any of its predecessors, subsidiaries or affiliates, and its
or their officers, partners, directors, trustees, agents, employees, attorneys,
successors and assigns (individually and in their representative capacities all
of the foregoing being referred to herein as the "Bank Releasees"), from and
with respect to any and all debts, claims, demands, and causes of action of any
kind whatsoever, whether known or unknown or unforeseen, which Mr. Wells now
has, ever had or may in the future have against the Bank Releasees, arising
prior to December 20, 2003, including without limitation on the foregoing those
arising out of or in any manner relating to Mr. Wells' employment by Berkshire
or the termination thereof.

            With respect to any rights Mr. Wells may have under the Age
Discrimination in Employment Act of 1967 or the Older Worker's Benefit
Protection Act, as presently in effect, which rights he is releasing under this
Agreement, Mr. Wells acknowledges that he has been given twenty-one (21) days to
consider this Agreement; that to the extent he has executed this Agreement prior
to the expiration of that period, he has done so knowingly and voluntarily; that

<PAGE>

for a period of seven (7) days following his execution of this Agreement, he may
revoke this Agreement; that this Agreement shall not become effective or
enforceable until such seven (7) day revocation period has expired; and that
Berkshire has no obligation to pay any sum or perform any act referred to in
this Agreement until the release contained in this Paragraph 2 becomes effective
and enforceable. Such revocation must be made by delivering a written notice of
revocation to Michael P. Daly, President and CEO, Berkshire Hills Bancorp., Inc.
and Berkshire Bank, and for such revocation to be effective, notice must be
received no later than 5:00 PM (EST) on the seventh (7th) calendar day after Mr.
Wells executes this Agreement.

      3. In consideration of the foregoing, Berkshire, and any and all of its
related or affiliated entities, and their respective officers, directors,
trustees, employees, agents, attorneys, predecessors, successors and assigns,
individually and in their representative capacities, release and forever
discharge, and covenant not to sue or commence or prosecute proceedings against
Mr. Wells, or any of his representatives, agents, attorneys, executors, assigns,
heirs and administrators (herein collectively the "Wells Releasees"), from and
with respect to any and all debts, claims, demands, damages and causes of action
of any kind whatsoever, whether known or unknown or unforeseen, which Berkshire
now has, ever had or may in the future have against the Wells Releasees, arising
prior to December 20, 2003, including without limitation on the foregoing, those
arising out of or in any manner relating to Mr. Wells' employment by Berkshire.

      4. Mr. Wells and Berkshire agree that they will treat each other
respectfully in any public comments and to that end they will not make any
negative, embarrassing or disparaging public statements, either verbal or
written, about each other.

      5. The parties hereto agree that the provisions, terms and conditions of
this Agreement and the Retirement Agreement attached hereto as Exhibit A are to
be held in strict confidence. Unless required by law or compelled by legal
process, Mr. Wells will not disclose or discuss the provisions, terms or
conditions of these agreements with any person, except his immediate family,
attorneys, accountants or other tax or financial advisors. Unless required by
law or compelled by legal or regulatory process, Berkshire agrees not to
disclose or discuss the provisions, terms or conditions of these agreements with
any person, including without limitation any Berkshire agent, servant or
employee; provided, however, that such disclosure may be made to persons,
including Berkshire's attorneys, accountants or other tax or financial advisors,
on a strict need-to-know basis only to the extent necessary to further a
specific and legitimate business interest of Berkshire.

      6. Neither anything contained herein, nor the payment of any sum provided
for herein, nor the performance of any act pursuant hereto shall be construed as
an admission by either party of any liability of any kind to the other party.

      7. This Agreement shall be binding upon Mr. Wells, Berkshire and their
respective heirs, administrators, representatives, executors, predecessors,
successors and assigns, and shall inure to the benefit of Mr. Wells, Berkshire,
the Wells Releasees, and the Bank Releasees, and each of them, and to their
respective heirs, administrators, representatives, executors, predecessors,
successors and assigns.

                                       2
<PAGE>

      8. This Agreement shall in all respects be interpreted, enforced and
governed by and under the laws of the Commonwealth of Massachusetts without
reference to its conflict of laws provisions.

            IN WITNESS WHEREOF, the parties hereto have executed this Agreement
as an instrument under seal all as of the day and year first above written.

WITNESS:                                    BERKSHIRE BANK

/s/ Gerald A. Denmark                     By /s/ Michael P. Daly
----------------------------                ------------------------------------
                                            Michael P. Daly, President and CEO

                                            BERKSHIRE HILLS BANCORP, INC.

/s/ Gerald A. Denmark                     By /s/ Michael P. Daly
----------------------------                ------------------------------------
                                            Michael P. Daly, President and CEO

/s/ Gerald A. Denmark                     /s/ Robert A. Wells
----------------------------              --------------------------------------
                                            Robert A. Wells

                                       3
<PAGE>
                                                                       Exhibit A

                                         As of June 26, 2003

Mr. Robert A. Wells
76 Lime Kiln Road
Lenox, MA 01240

Dear Bob:

      As we have discussed, this is to confirm that you have decided to retire
as Chairman of the Board of Berkshire Hills Bancorp, Inc. (the "Holding
Company") and Berkshire Bank ("Berkshire Bank") (collectively, "Berkshire") and
as Chairman and Principal Executive of each of Berkshire Hills Foundation and
Greater Berkshire Foundation, Inc. (the "Foundations") effective on the earlier
of (a) December 31, 2003 or (b) such other date as you shall elect upon notice
to me ("Your Retirement Date"). In recognition of your years of service,
Berkshire agrees to the following:

      1. You shall be a director of the Holding Company and Berkshire Bank until
the expiration of your current term in 2004, and thereafter as you are
re-nominated and re-elected. So long as you are a director, you will be a member
of various Berkshire committees to which you are appointed and a director of
each of the Foundations.

      2. After Your Retirement Date, and so long as you are a director of the
Holding Company, you will receive stock awards and options, if any, on the same
basis that they are granted to all other independent directors.

      3. Within 30 days after Your Retirement Date, but in any event no later
than December 31, 2003, you will receive a lump sum payment of $200,000.00, less
all required and necessary deductions and withholdings. All salary and other
payments from Berkshire and the Foundations, other than as set forth in this
letter, will cease as of Your Retirement Date. You will retain all of your
presently vested and unvested stock options and awards. If you are not
re-elected to the Holding Company's Board, you will be appointed to its Advisory
Board for a term sufficient to vest all of your unvested stock options and
awards. If you are not re-elected to the Holding Company's Board of Directors
and if, for any reason, the Advisory Board does not exist at that time, then all
of your unvested stock options and awards will immediately vest.

      4. You are entitled to certain benefits under the executive supplemental
compensation agreement with Berkshire Bank dated November 7, 1995 and a trust
agreement dated May 31, 1996 between Berkshire Bank and State Street Bank and
Trust Company. Berkshire Bank will hire, at its expense, a mutually agreeable,
independent pension actuarial firm (the "Actuary") to calculate, within 30 days
of Your Retirement Date, all benefits due to you under the agreements. If
appropriate, the amounts heretofore funded by Berkshire Bank and held under said
agreements at State Street Bank and Trust Company will be further funded to
satisfy

<PAGE>

Mr. Robert A. Wells
As of June 26, 2003
Page 2

Berkshire Bank's obligations to you thereunder, or, if overfunded, the
amount by which it is overfunded will be retained by Berkshire Bank. Said
calculation by the Actuary will be final and binding on the parties, but each
party will have the right to review all assumptions and methods of calculation
prior to said calculation becoming final.

      5. Until November 22, 2005, you shall have:

            A. Use of your automobile, with Berkshire Bank paying all automobile
expenses on the same basis that it presently does; and on or about that date,
Berkshire Bank will transfer title of that vehicle to you.

            B. Use of your current office until December 31, 2003; and
thereafter, use of either your existing office or the second floor Board Room.

            C. Continued coverage under Berkshire Bank's existing regular, or
upon you and/or your spouse attaining age 65, MEDEX group medical and dental
insurance plans, as those plans shall hereafter be modified for all eligible
employees. You will continue to be responsible for your premium co-payments, the
amount of which will be billed by Berkshire to you periodically.

      6. Your employment by Berkshire and your engagement as an independent
contractor by the Foundations shall be deemed terminated as of Your Retirement
Date.

      7. You will continue to own the Royal Macabees (now Reassure America)
Policy (No. 4052-202). You will refund payments made by Berkshire on your behalf
by making a payment to Berkshire of $20,500.00 on or before Your Retirement
Date.

                                       2
<PAGE>

Mr. Robert A. Wells
As of June 26, 2003
Page 3

      Please sign below to signify your agreement with the foregoing, and I will
then ask the Boards of Directors of Berkshire to affirm this agreement.

                                          Very truly yours,

                                          BERKSHIRE HILLS BANCORP, INC. and
                                          BERKSHIRE BANK

                                       By: /s/ Michael P. Daly
                                          --------------------------------------
                                          Michael P. Daly, President and CEO

                                          AGREED TO:

                                          /s/ Robert A. Wells
                                          --------------------------------------
                                          Robert A. Wells

                                          THIS LETTER AGREEMENT IS AFFIRMED:

                                          BERKSHIRE HILLS BANCORP, INC.

                                       By: /s/ Catherine B. Miller
                                          --------------------------------------
                                          On behalf of its Board of Directors

                                          BERKSHIRE BANK

                                       By: /s/ Catherine B. Miller
                                          --------------------------------------
                                          On behalf of its Board of Directors

                                       3

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