Document:

Exhibit 10.1

Exhibit 10.1

CONFIDENTIAL – HAND DELIVERED

April 19, 2010

David B. Farrell

210 Rote Hill Road

Sheffield, MA 01257

Dear Dave:

For the reasons that we have discussed, you have elected to terminate your employment with the
Company (as hereinafter defined) effective April 30, 2010. Berkshire Hills Bancorp, Inc., together
with its primary subsidiaries Berkshire Bank and Berkshire Insurance Group, Inc., desires to
resolve any and all issues relating to the conclusion of your employment with the Company amicably
and on mutually satisfactory terms. To that end, the Company is offering you a separation package
in accordance with the terms of this Letter Agreement. Upon your signature, this Letter Agreement
shall constitute the agreement between you and the Company on the terms of your separation from
employment as follows:

1. Your employment shall terminate effective April 30, 2010 (the “Termination Date”). You shall be
paid your earned salary through April 16, 2010 and thereafter paid all remaining unused vacation
time through the Termination Date. It is understood that you shall take vacation time during the
last two weeks prior to the Termination Date.

2. Although you are not otherwise entitled to it, in consideration of your acceptance of this
Letter Agreement, the Company shall provide you with a Separation Payment in the gross amount of
$125,000.00 (the “Separation Pay”), less legally required withholdings. Your Separation Pay shall
be made in six equal monthly installments (each in the gross amount of $20,833.34) beginning on the
first regularly-scheduled Company pay date following eight days after which you execute this Letter
Agreement and return it to the Company without revocation. As well, you understand and agree that
from the date of this Letter Agreement through the Termination Date and during the period in which
you are entitled to receive installment payments of the Separation Pay, you may be called upon by
the Company to provide transitional assistance. Payment of each monthly installment of the
Separation Pay shall be contingent on your performance of all obligations and undertakings you have
agreed to in this Letter Agreement. The parties have agreed that any stock awards given to you
under the terms of that certain “Berkshire Hills Bancorp, Inc. 2003 Equity Compensation Plan
Restricted Stock Award Agreement” signed by you as a Director of the Company under an Award Date
of January 30, 2008 will continue to vest through 1/30/2011; however, you agree that you will
forfeit the additional, as yet undocumented stock award granted to you as an employee of the
Company as of January 30, 2010, as of the Termination Date and all of your rights to any unvested
stock under such 2010 award are null and void. No Company contribution or match shall be made to
the Company’s 401(k) Plan on account of the Separation Pay or otherwise after the Termination Date.
You also agree that any and all Change in Control Agreements entered into between you
and the Company shall also become null and void and of no further recourse to either party as of
the Termination Date.

 

 

 

3. The Company also agrees to provide you with group health and dental insurance coverage, if
applicable, through April 30, 2010. After that date, you shall be entitled to receive extended
health coverage through the Company, at your own expense, at whatever premium the Company is
permitted to charge by law and for whatever period is provided by law. You shall receive further
information concerning your rights under the Consolidated Omnibus Reconciliation Act of 1985, as
amended (“COBRA”).

4. Other than the obligations of the Company as set forth under the terms of paragraphs 2 and 3 of
this Letter Agreement, you represent and agree that you are not entitled to any other wages,
salary, bonuses, benefits or any other compensation or reimbursements from the Company.

5. As is standard in situations where an employer is paying an employee additional compensation
upon separation, you agree to waive and release and promise never to assert any and all claims that
you have or might have against the Company, arising from and related to your employment with and/or
separation from the Company. For purposes of this Letter Agreement, the term “Company” means and
includes Berkshire Bank, Berkshire Insurance Group, Inc. and Berkshire Hills Bancorp, Inc., their
predecessors and successors, all of their past, present, and future shareholders, trustees,
directors, officers, employees, representatives, attorneys, agents and assigns, and all of their
parent or controlling corporations, and their affiliates and subsidiaries, or any other legal
entity describing Berkshire Bank, Berkshire Insurance Group, Inc. and Berkshire Hills Bancorp
Inc.’s organization or through which they conduct business.

6. You represent and warrant that you have not filed any complaints, charges or claims against the
Company with any local, state or federal court or administrative agency. Except with respect to
any rights arising out of this Letter Agreement and any rights that you may have to unemployment
compensation, you specifically agree that you waive and release any and all manner of claims you
ever had, now have or may have under any federal or state labor, employment, retaliation or
discrimination laws, statutes, public policies, orders or regulations, including, but not limited
to, Title VII of the Civil Rights Act of 1964, as amended, the Equal Pay Act of 1963, as amended,
the Employee Retirement Income Security Act of 1974, as amended, the Occupational Safety and Health
Act of 1970, as amended, the Rehabilitation Act of 1973, as amended, the Fair Labor Standards Act
of 1938, as amended, the Americans with Disabilities Act of 1990, as amended, the Family and
Medical Leave Act of 1993, as amended, the Age Discrimination in Employment Act, as amended,
Chapters 149 through 154 of the Massachusetts General Laws, the Massachusetts Civil Rights Act, the
Massachusetts Equal Rights Law, or at common law, including but not limited to claims relating to
breach of an oral or written contract, wrongful discharge, misrepresentation, defamation,
interference with prospective economic advantage, interference with contractual relationship,
intentional and negligent infliction of emotional distress, negligence, breach of the covenant of
good faith and fair dealing and any claims under the Restricted Stock Agreement. It is expressly
agreed and understood that the release contained herein is a GENERAL RELEASE, but that you are not
waiving or releasing any rights or claims that arise after the date that this Letter Agreement is
executed. The consideration given by the Company in exchange for your General Release exceeds
anything of value to which you otherwise were entitled in the absence of a waiver.

 

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7. Release of ADEA Claims. Not in limitation of the previous paragraph, by signing this
Letter Agreement, you agree and understand that you are waiving, relinquishing and releasing any
and all claims or
rights that you have or may have against the Company arising under the Age Discrimination in
Employment Act, 29 U.S.C. § 621 et seq., and its state law equivalent. You are not, however,
waiving any rights or claims that may arise after the execution of this Letter Agreement. You
specifically acknowledge that this waiver and release releases the Company from liability to you
for any alleged violation of the ADEA to the date of this Letter Agreement.

8. With respect to the rights and claims that you are waiving, you are waiving not only your right
to recover in an action that you might commence, but also your right to recover in any action
brought on your behalf by any other party, including, but not limited to, the U.S. Equal Employment
Opportunity Commission, or any other federal, state or local governmental agency or department.
Nothing in this Letter Agreement shall be construed to affect the rights and responsibilities of
the Equal Employment Opportunity Commission (“EEOC”) and the Massachusetts Commission Against
Discrimination (“MCAD”) to enforce the anti-discrimination laws. Also, nothing in this Letter
Agreement may be used to justify interfering with the employee’s protected right to file a charge
or participate in an investigation or proceeding conducted by the EEOC or MCAD. In addition, and
not in limitation of the foregoing, you hereby forever release and discharge the Company from any
liability or obligation to reinstate or reemploy you in any capacity.

9. By executing this Letter Agreement, you agree to keep the terms of this document confidential.
However, nothing in this Letter Agreement shall prohibit you from disclosing such confidential
information (i) to your counsel and accountants; (ii) to your spouse; (iii) to government
authorities requesting such information; and (iv) as otherwise required by law. You also
acknowledge and agree that you have been the recipient of confidential and proprietary business
information and you agree that you will not use or disclose such confidential and proprietary
information except as may be expressly permitted by the Company in writing or as may be required by
law.

10. You further agree to return all Company documents and other Company property immediately upon
request by the Company. You also agree to cooperate with the Company to the extent that your
knowledge of facts concerning the Company’s business is required for any court or administrative
proceeding. The Company agrees not to contest any claim for unemployment benefits filed by you so
long as you do not state any other claims against the Company in the process of seeking
unemployment benefits. You agree that the Company has provided you with the Massachusetts Division
of Unemployment Assistance pamphlet entitled “How To File For Unemployment Insurance Benefits”.

11. You agree not to make any disparaging statements concerning the Company, its affiliates or
current or former officers, directors, employees or agents and further agree not to take any
actions or conduct which would reasonably be expected to affect adversely the reputation or
goodwill of the Company or any of its affiliates or any of its current or former officers,
directors, employees or agents. The Company’s current President and CEO, Executive Vice Presidents
and Senior Vice Presidents also shall not make any disparaging statements concerning you nor shall
they take any actions or engage in conduct which would reasonably be expected to affect adversely
your reputation. The provisions of this paragraph shall not apply to any truthful statement
required to be made by you or the Company in any legal proceeding or governmental or regulatory
investigation.

12. You agree to execute and be bound by the terms and conditions set forth on the Non-Competition
and Non-Solicitation Agreement, attached hereto as Exhibit A and incorporated herein. You shall
execute
and deliver a signed original of Exhibit A to the Company simultaneously with your delivery of a
signed original of this Letter Agreement.

 

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13. You acknowledge and agree that the restrictions set forth in this Letter Agreement and in
Exhibit A are reasonable and necessary in order to protect the good will and legitimate business
interests of the Company and that any violation thereof would likely result in irreparable injury
to the Company. You therefore agree that, in the event of a violation or threatened violation of
any of the restrictions on conduct by you contained in this Letter Agreement and/or Exhibit A, the
Company shall be entitled to obtain from any court of competent jurisdiction preliminary and
permanent injunctive relief, in addition to any other rights or remedies.

14. In addition to the remedies provided in this Letter Agreement, Exhibit A and otherwise
available at law or in equity, in the event of any breach by you of the restrictions contained in
this Letter Agreement and Exhibit A, the Company shall have the right (and the exercise of such
right shall not constitute an election of remedies) to recover from you the amount of any portion
of the Separation Pay that shall have been paid to you under this Letter Agreement and cease all
future installment payments of the Separation Pay, in which event you shall be deemed to have
forfeited (as liquidated damages and not a penalty) your right to the Separation Pay, and the
Company also shall have the right to recover the reasonable fees and disbursements of its counsel
incurred in connection with the pursuit of any and all remedies pertaining to such breach or
impending breach.

15. If the Company shall exercise its rights under the previous paragraph of this Letter Agreement,
then the Letter Agreement and Exhibit A shall remain in full force and effect and the obligations
imposed upon you in both documents shall continue.

16. You acknowledge that you will have twenty-one (21) days from receipt within which to consider
whether or not it is in your best interest to accept this offer and sign this Letter Agreement and
that you may rescind it within seven days of the day you sign it, after which time it becomes
unrevokable. Prior to executing this Letter Agreement, I advise you to consult with an attorney
before signing this Letter Agreement. By signing this Letter Agreement, you represent that you
have carefully read this document, that you understand it, and that you have had an opportunity to
consult with and review this with an attorney of your choice. You also represent that you know and
understand the contents of this Letter Agreement, including its final and binding effect on your
rights and duties, and that you freely and voluntarily assent to all the terms and conditions with
the full intent of releasing the Company from all claims. You represent that the only
consideration for signing this Letter Agreement are the terms stated herein; that no other
promises, representations or agreements of any kind have been made to or with you to cause you to
sign this Letter Agreement. You represent that your waivers are in exchange for extra
consideration to which you would not have been entitled in the absence of the waivers. You further
acknowledge and agree that the Company is not undertaking to advise you with respect to any tax
consequences of this Letter Agreement and that you are solely responsible for determining those
consequences.

17. This Letter Agreement shall become effective and enforceable the eighth day after you have
executed the document and delivered it to the Company. A stamped-return envelope is enclosed for
your convenience. You understand that you have the right to revoke this Letter Agreement at any
time within that period. If you choose to revoke, this Letter Agreement may only be revoked in its
entirety. Once revoked, no provision of this Letter Agreement shall be enforceable.

 

4

 

18. You acknowledge that the payments and benefits described in this Letter Agreement constitute a
special separation benefit which the Company is providing in its discretion due to your unique
circumstances and that you are not otherwise entitled to receive this entire separation package
from the company.

19. We agree and specifically acknowledge that we are entering into this Letter Agreement for the
purpose of amicably resolving any and all issues relating to the conclusion of, or any other matter
related to your employment with the Company. This Letter Agreement supersedes any previous
agreement, whether written or oral, that you may have had with the Company and any other agreement
is merged into and extinguished by this Letter Agreement. This Letter Agreement shall not be
deemed an admission by the Company of a violation of any statute or law or wrongdoing of any kind.

20. The terms of this Agreement are contractual in nature and not a mere recital, and it shall take
effect as a sealed document. This Agreement shall be governed by and construed in accordance with
the laws of the Commonwealth of Massachusetts, without reference to conflict of law rules, and this
Agreement shall be deemed to be executed and performed in Massachusetts and shall be enforceable
only in the Massachusetts courts.

If you are in agreement with the terms of severance set forth above, please indicate by executing a
copy of this letter and returning it to me.

 

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	BERKSHIRE HILLS BANCORP, INC.

 	 
	By:  	/s/ Linda A. Johnston
 	 
	 	 	Linda A. Johnston 	 
	 	 	SVP Human Resources 	 

I understand and agree completely to the

foregoing as of April 19, 2010

	 	 	 	 	 
	/s/ David B. Farrell
 	 
	David B. Farrell 	 

Witness:                                                             

 

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EXHIBIT A

NON-SOLICITATION AND NON-COMPETITION AGREEMENT

This Non-Solicitation and Non-Competition Agreement (this “Agreement”) dated April 19, 2010
between BERKSHIRE HILLS BANCORP, INC., a Delaware corporation with a principal place of business
located in Pittsfield, Massachusetts and DAVID B. FARRELL of Sheffield, Massachusetts (“Farrell”).

PRELIMINARY STATEMENT

The Company (defined for purposes of this Agreement to mean and include Berkshire Hills
Bancorp, Inc., together with its primary subsidiaries Berkshire Bank and Berkshire Insurance Group,
Inc., their predecessors and successors, all of their past, present, and future shareholders,
trustees, directors, officers, employees, representatives, attorneys, agents and assigns, and all
of their parent or controlling corporations, and their affiliates and subsidiaries, or any other
legal entity describing Berkshire Bank, Berkshire Insurance Group, Inc. and Berkshire Hills Bancorp
Inc.’s organization or through which they conduct business) and Farrell are parties to a Letter
Agreement of even date herewith (the “Separation Agreement”), which is incorporated herein by
reference; and

Pursuant to the terms of the Separation Agreement, the Company has agreed to pay Farrell
Separation Pay in the gross amount of $125,000, less customary payroll taxes and deductions; and

Pursuant to the terms of the Separation Agreement, Farrell has agreed to enter into a this
Agreement in partial consideration for the Company’s agreement to pay Farrell the Separation Pay;
and

The duration of this Agreement is six (6) months from the Termination Date set forth in the
Separation Agreement; provided, however, that notwithstanding anything else herein to the contrary
Farrell’s obligations under Section 3 of this Agreement shall continue in perpetuity; and

Farrell agrees and acknowledges that by virtue of his position in the Company, he is familiar
with and in possession of the Company’s trade secrets, customer information, and other confidential
information which are valuable to the Company, and that their goodwill, protection, and maintenance
constitute a legitimate business interest of the Company, to be protected by the non-competition
restrictions set forth herein. Farrell agrees and acknowledges that the non-competition
restrictions set forth in this Agreement are reasonable and necessary and do not impose undue
hardship or burdens on him.

NOW, THEREFORE, in consideration of the mutual covenants contained herein and other good and
valuable consideration, the receipt and sufficiency of which are hereby acknowledged, the parties
hereto hereby agree as follows:

 

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1. Non-Competition.

(a) Farrell hereby agrees that, beginning on May 1, 2010 and for a period of 6 months
thereafter — until October 31, 2010 – (the “Non-Competition Period”), Farrell shall not, directly
or indirectly own, manage, operate, join, be employed by, perform services, consulting or other
work for, or provide any assistance to (the “Prohibited Activities”), any corporation, partnership,
or other entity or person which owns, manages, operates, controls, participates in the ownership,
management, operation or control of, is employed by, performs services or other work for, provides
any assistance to, is engaged with respect to any banking, insurance, wealth management or
financial services business including, but not limited to, banks, insurance businesses or credit
unions, which engages in such banking, insurance, wealth management or financial services business
and has an office or offices located within (a) any of the following Massachusetts counties:
Berkshire, Hampshire, Hampden and Franklin; (b) any of the following New York Counties: Albany,
Oneida, Saratoga, Rensselaer and Schenectady; and/or (c) any of the following Vermont counties:
Bennington, Rutland and Windsor (a “Competitor Employer”).

(b) Farrell acknowledges that he has carefully read and considered the provisions of this
Agreement and, having done so, agrees that the restrictions set forth herein and the geographic
areas of restriction are fair and reasonable and are reasonably required for the protection of the
interests of the Company.

(c) In the event that the provisions of this Agreement relating to the time periods and/or
geographic areas of restriction shall be declared by a court of competent jurisdiction to exceed
the maximum time period or areas that such court deems reasonable and enforceable, the time period
and/or geographic areas of restriction deemed reasonable and enforceable by the court shall become
and thereafter be the maximum time period and/or geographic areas under this Agreement.

(d) In the event that a Competitor Employer contacts Farrell for the purpose of requesting
that Farrell engage in Prohibited Activities with a Competitor Employer during the Non-Competition
Period, Farrell may request that the Company waive the provisions of Section 1(a) of this
Agreement. The Company shall consider Farrell’s request for a waiver, but is under no obligation
to grant the waiver. The Company shall have absolute and sole discretion to decide whether or not
to grant the waiver. If, in its absolute and sole discretion, the Company decides to grant the
waiver request, the waiver shall not become effective until Farrell and the Company shall have
entered into a written modification of this Agreement, signed by both parties.

2. Non-Solicitation. Farrell hereby agrees that, beginning on May 1, 2010 and for a
period of 6 months thereafter — ending on October 31, 2010 — Farrell will not, directly or
indirectly, on his own behalf or on behalf of any third person or entity, and whether through his
own efforts or through the efforts or assistance of any other person or entity (including, without
limitation, any person employed by or associated with any entity with whom he is or may become
employed or associated):

(a) Solicit or accept any banking, insurance, wealth management or financial services business
from (i) any individual or entity that was a client or customer of the Company at any time during
the six (6) months immediately prior to the end of Farrell’s employment with the Company, or (ii)
any individual or entity that was a prospect of the Company at any time during the twelve (12)
months
immediately prior to the end of Farrell’s employment with the Company, if he directly
solicited such prospect or if he directly or indirectly, in whole or in part, supervised or
participated in solicitation activities related to such prospect; provided, however, that Farrell
may accept employment with a Company client or customer or prospect that is not a Competitor
Employer; or

 

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(b) Participate in hiring, hire or employ an employee or consultant of the Company, or
solicit, encourage or induce any such employee or consultant to terminate his or her employment or
other relationship with the Company;

(c) Interfere with any relationship, contractual or otherwise, between the Company and any
other party, including, without limitation, any supplier or vendor of the Company, or solicit such
party to discontinue or reduce its business with the Company.

Farrell also agrees that for a period of six (6) months after his employment with the Company
ends, he will inform his potential and actual future employers of his obligations under this
Agreement.

3. Protection and Non-Disclosure of Confidential Information. Farrell hereby agrees
and acknowledges that his employment with the Company has created a continuing relationship of
confidence and trust between Farrell and the Company with respect to Confidential Information.
Farrell hereby warrants and agrees that he will keep in confidence and trust at all times after his
employment with the Company shall terminate all Confidential Information known to him, and will not
use or disclose such Confidential Information without the prior written consent of the Company.
Nothing in this Agreement is intended to or shall preclude Farrell from providing truthful
testimony or providing truthful information in response to a valid subpoena, court order or request
of any federal, state or local regulatory or quasi-regulatory authority; provided, however, that,
to the extent permitted by law, Farrell has first provided to the Company as much advance notice as
practicable of any such compelled disclosure, and further that Farrell agrees to honor any order or
ruling obtained by the Company quashing or barring any such subpoena, court order or request for
disclosure. As used in this Agreement, “Confidential Information” means any and all information
belonging to the Company, which is of value to the Company and the disclosure of which could result
in a competitive or other disadvantage to the Company. Examples of Confidential Information are,
without limitation, financial information, reports and forecasts; trade secrets, know-how and other
intellectual property; software; market or sales information or plans; customer lists and
information; business plans, prospects and opportunities; and possible acquisitions or dispositions
of businesses or facilities that have been discussed by the management of the Company.
Confidential Information includes information Farrell developed or learned in the course of his
employment with and service as a director of the Company, as well as other information to which
Farrell may have had access in connection with his employment or service as a director.
Confidential Information also includes the confidential information of others, including, but not
limited to, customers of the Company, with whom the Company has a business relationship.
Notwithstanding the foregoing, Confidential Information does not include information in the public
domain, unless such information entered the public domain due to a breach of Farrell’s obligations
under this Agreement regarding Confidential Information or otherwise.

4. Consideration. As consideration for the obligations of Farrell hereunder, the
Company shall satisfy its obligations to Farrell as described in the Separation Agreement.

 

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5. Defaults. Farrell shall be deemed to be in default of his obligations under this
Agreement (a “Default”), if Farrell shall have breached his obligations under Section 1 hereof and
such breach shall continue for 15 days after the Company has given Farrell notice of same.
Notwithstanding anything to the contrary contained in the foregoing sentence, Farrell shall be
deemed to be in default of his obligations under this Agreement (also a “Default”) immediately upon
any breach of his obligations under Sections 2 and 3 hereof, and the Company shall not be obligated
to provide any notice thereof or cure period.

6. Remedies.

(a) Farrell acknowledges that in the event of an actual or threatened Default, the Company’s
remedies at law will be inadequate. Accordingly, the Company shall be entitled, at its election,
to enjoin any actual or threatened Default, and/or to obtain specific performance of Farrell’s
obligations under this Agreement without the necessity of showing any actual damage or the
inadequacy of monetary damages. Any such equitable remedy shall not constitute the sole and
exclusive remedy for any such Default, and the Company shall be entitled to pursue any other
remedies at law or in equity. In the event of a Default by Farrell, the Company shall be entitled
to (a) recover from Farrell its costs, including reasonable attorneys’ fees, incurred in enforcing
its rights under this Agreement and (b) cease making payments to Farrell under paragraph 2 of the
Separation Agreement without invalidating any portion of the Separation Agreement or this
Agreement.

(b) Any court proceeding to enforce this Agreement may be commenced by either party in the
Berkshire Superior Court, Pittsfield, Commonwealth of Massachusetts. The parties hereto submit to
the exclusive jurisdiction of such court and waive any objection which they may have to the pursuit
of any such proceeding in such court.

7. Entire Agreement. This Agreement, together with the Separation Agreement,
constitutes the entire agreement between the parties relating to the subject matter hereof and
supersedes any and all previous agreements, oral and written, between the parties with respect to
the subject matter hereof.

8. Non-Waiver. The failure by a party in one or more instances to insist upon
performance of any of the terms, covenants or conditions of this Agreement, or to exercise any
rights or privileges conferred in this Agreement, or the seek enforcement of any of the terms,
covenants or conditions of this Agreement following any breach of any of the terms, covenants,
conditions, rights or privileges, shall non constitute, nor be deemed to constitute, a waiver of
any of the terms, covenants or conditions of this Agreement, but the same shall continue and remain
in full force and effect as if no such failure or forbearance had occurred. No waiver of the
terms, covenants or conditions of this Agreement shall be effective unless it is in writing and
signed by an authorized representative of the waiving party.

9. Applicable Law. This Agreement shall be governed and controlled as to validity,
enforcement, interpretation, construction, effect and in all other respects by the internal laws of
the Commonwealth of Massachusetts applicable to contracts made and wholly to be performed in the
Commonwealth.

 

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10. Binding Effect; Benefit. This Agreement shall inure to the benefit of and be
binding upon the parties hereto and their respective successors, assigns, heirs and personal
representatives. Nothing in this Agreement, express or implied, is intended to confer on any
person other than the parties hereto and
their respective successors, assigns, heirs and personal representatives any rights, remedies,
obligations or liabilities under or by reason of this Agreement.

11. Amendments. This Agreement shall not be modified or amended except pursuant to an
instrument in writing executed and delivered on behalf of each of the parties hereto.

12. Severability. Any term or provision of this Agreement that is invalid or
unenforceable in any situation in any jurisdiction shall not affect the validity or enforceability
of the remaining terms and provisions hereof or the validity or enforceability of the offending
term or provision in any other situation or in any other jurisdiction. If the final judgment of a
court of competent jurisdiction declares that any term or provision hereof is invalid or
unenforceable, the parties hereto agree that the court making the determination of invalidity or
unenforceability shall have the power to reduce the scope, duration, or area of the term or
provision, to delete specific words or phrases, or to replace any invalid or unenforceable term or
provision with a term or provision that is valid and enforceable and that comes closest to
expressing the intention of the invalid or unenforceable term or provision, and this Agreement
shall be enforceable as so modified after the expiration of the time within which the judgment may
be appealed.

13. Counterparts. This Agreement may be executed in any number of counterparts, each
of which shall be deemed an original and all of which together shall constitute one and the same
instrument.

IN WITNESS WHEREOF, the parties hereto have executed this Agreement as a sealed instrument as
of the date first above written.

	 	 	 	 	 
	 	 	 
	 	DAVID B. FARRELL 	 
	 	 	 	 
	 	BERKSHIRE HILLS BANCORP, INC.,

 	 
	 	By:  	 	 
	 	 	Its 	 

 

11Exhibit 10.2

Exhibit 10.2

NON-SOLICITATION AND NON-COMPETITION AGREEMENT

This Non-Solicitation and Non-Competition Agreement (this “Agreement”) dated April 19, 2010
between BERKSHIRE HILLS BANCORP, INC., a Delaware corporation with a principal place of business
located in Pittsfield, Massachusetts and DAVID B. FARRELL of Sheffield, Massachusetts (“Farrell”).

PRELIMINARY STATEMENT

The Company (defined for purposes of this Agreement to mean and include Berkshire Hills
Bancorp, Inc., together with its primary subsidiaries Berkshire Bank and Berkshire Insurance Group,
Inc., their predecessors and successors, all of their past, present, and future shareholders,
trustees, directors, officers, employees, representatives, attorneys, agents and assigns, and all
of their parent or controlling corporations, and their affiliates and subsidiaries, or any other
legal entity describing Berkshire Bank, Berkshire Insurance Group, Inc. and Berkshire Hills Bancorp
Inc.’s organization or through which they conduct business) and Farrell are parties to a Letter
Agreement of even date herewith (the “Separation Agreement”), which is incorporated herein by
reference; and

Pursuant to the terms of the Separation Agreement, the Company has agreed to pay Farrell
Separation Pay in the gross amount of $125,000, less customary payroll taxes and deductions; and

Pursuant to the terms of the Separation Agreement, Farrell has agreed to enter into a this
Agreement in partial consideration for the Company’s agreement to pay Farrell the Separation Pay;
and

The duration of this Agreement is six (6) months from the Termination Date set forth in the
Separation Agreement; provided, however, that notwithstanding anything else herein to the contrary
Farrell’s obligations under Section 3 of this Agreement shall continue in perpetuity; and

Farrell agrees and acknowledges that by virtue of his position in the Company, he is familiar
with and in possession of the Company’s trade secrets, customer information, and other confidential
information which are valuable to the Company, and that their goodwill, protection, and maintenance
constitute a legitimate business interest of the Company, to be protected by the non-competition
restrictions set forth herein. Farrell agrees and acknowledges that the non-competition
restrictions set forth in this Agreement are reasonable and necessary and do not impose undue
hardship or burdens on him.

 

 

 

NOW, THEREFORE, in consideration of the mutual covenants contained herein and other good and
valuable consideration, the receipt and sufficiency of which are hereby acknowledged, the parties
hereto hereby agree as follows:

1. Non-Competition.

(a) Farrell hereby agrees that, beginning on May 1, 2010 and for a period of 6 months
thereafter — until October 31, 2010 — (the “Non-Competition Period”), Farrell shall not, directly
or indirectly own, manage, operate, join, be employed by, perform services, consulting or other
work for, or provide any assistance to (the “Prohibited Activities”), any corporation, partnership,
or other entity or person which owns, manages, operates, controls, participates in the ownership,
management, operation or control of, is employed by, performs services or other work for, provides
any assistance to, is engaged with respect to any banking, insurance, wealth management or
financial services business including, but not limited to, banks, insurance businesses or credit
unions, which engages in such banking, insurance, wealth management or financial services business
and has an office or offices located within (a) any of the following Massachusetts counties:
Berkshire, Hampshire, Hampden and Franklin; (b) any of the following New York Counties: Albany,
Oneida, Saratoga, Rensselaer and Schenectady; and/or (c) any of the following Vermont counties:
Bennington, Rutland and Windsor (a “Competitor Employer”).

(b) Farrell acknowledges that he has carefully read and considered the provisions of this
Agreement and, having done so, agrees that the restrictions set forth herein and the geographic
areas of restriction are fair and reasonable and are reasonably required for the protection of the
interests of the Company.

(c) In the event that the provisions of this Agreement relating to the time periods and/or
geographic areas of restriction shall be declared by a court of competent jurisdiction to exceed
the maximum time period or areas that such court deems reasonable and enforceable, the time period
and/or geographic areas of restriction deemed reasonable and enforceable by the court shall become
and thereafter be the maximum time period and/or geographic areas under this Agreement.

(d) In the event that a Competitor Employer contacts Farrell for the purpose of requesting
that Farrell engage in Prohibited Activities with a Competitor Employer during the Non-Competition
Period, Farrell may request that the Company waive the provisions of Section 1(a) of this
Agreement. The Company shall consider Farrell’s request for a waiver, but is under no obligation
to grant the waiver. The Company shall have absolute and sole discretion to decide whether or not
to grant the waiver. If, in its absolute and sole discretion, the Company decides to grant the
waiver request, the waiver shall not become effective until Farrell and the Company shall have
entered into a written modification of this Agreement, signed by both parties.

2. Non-Solicitation. Farrell hereby agrees that, beginning on May 1, 2010 and for a
period of 6 months thereafter — ending on October 31, 2010 — Farrell will not, directly or
indirectly, on his own behalf or on behalf of any third person or entity, and whether through his
own efforts or through the efforts or assistance of any other person or entity (including, without
limitation, any person employed by or associated with any entity with whom he is or may become
employed or associated):

(a) Solicit or accept any banking, insurance, wealth management or financial services business
from (i) any individual or entity that was a client or customer of the Company at
any time during the six (6) months immediately prior to the end of Farrell’s employment with
the Company, or (ii) any individual or entity that was a prospect of the Company at any time during
the twelve (12) months immediately prior to the end of Farrell’s employment with the Company, if he
directly solicited such prospect or if he directly or indirectly, in whole or in part, supervised
or participated in solicitation activities related to such prospect; provided, however, that
Farrell may accept employment with a Company client or customer or prospect that is not a
Competitor Employer; or

 

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(b) Participate in hiring, hire or employ an employee or consultant of the Company, or
solicit, encourage or induce any such employee or consultant to terminate his or her employment or
other relationship with the Company;

(c) Interfere with any relationship, contractual or otherwise, between the Company and any
other party, including, without limitation, any supplier or vendor of the Company, or solicit such
party to discontinue or reduce its business with the Company.

Farrell also agrees that for a period of six (6) months after his employment with the Company
ends, he will inform his potential and actual future employers of his obligations under this
Agreement.

3. Protection and Non-Disclosure of Confidential Information. Farrell hereby agrees
and acknowledges that his employment with the Company has created a continuing relationship of
confidence and trust between Farrell and the Company with respect to Confidential Information.
Farrell hereby warrants and agrees that he will keep in confidence and trust at all times after his
employment with the Company shall terminate all Confidential Information known to him, and will not
use or disclose such Confidential Information without the prior written consent of the Company.
Nothing in this Agreement is intended to or shall preclude Farrell from providing truthful
testimony or providing truthful information in response to a valid subpoena, court order or request
of any federal, state or local regulatory or quasi-regulatory authority; provided, however, that,
to the extent permitted by law, Farrell has first provided to the Company as much advance notice as
practicable of any such compelled disclosure, and further that Farrell agrees to honor any order or
ruling obtained by the Company quashing or barring any such subpoena, court order or request for
disclosure. As used in this Agreement, “Confidential Information” means any and all information
belonging to the Company, which is of value to the Company and the disclosure of which could result
in a competitive or other disadvantage to the Company. Examples of Confidential Information are,
without limitation, financial information, reports and forecasts; trade secrets, know-how and other
intellectual property; software; market or sales information or plans; customer lists and
information; business plans, prospects and opportunities; and possible acquisitions or dispositions
of businesses or facilities that have been discussed by the management of the Company.
Confidential Information includes information Farrell developed or learned in the course of his
employment with and service as a director of the Company, as well as other information to which
Farrell may have had access in connection with his employment or service as a director.
Confidential Information also includes the confidential information of others, including, but not
limited to, customers of the Company, with whom the Company has a business relationship.
Notwithstanding the foregoing, Confidential Information does not include information in the public
domain, unless such information entered the public domain due to a breach of Farrell’s obligations
under this Agreement regarding Confidential Information or otherwise.

 

3

 

4. Consideration. As consideration for the obligations of Farrell hereunder, the
Company shall satisfy its obligations to Farrell as described in the Separation Agreement.

5. Defaults. Farrell shall be deemed to be in default of his obligations under this
Agreement (a “Default”), if Farrell shall have breached his obligations under Section 1 hereof and
such breach shall continue for 15 days after the Company has given Farrell notice of same.
Notwithstanding anything to the contrary contained in the foregoing sentence, Farrell shall be
deemed to be in default of his obligations under this Agreement (also a “Default”) immediately upon
any breach of his obligations under Sections 2 and 3 hereof, and the Company shall not be obligated
to provide any notice thereof or cure period.

6. Remedies.

(a) Farrell acknowledges that in the event of an actual or threatened Default, the Company’s
remedies at law will be inadequate. Accordingly, the Company shall be entitled, at its election,
to enjoin any actual or threatened Default, and/or to obtain specific performance of Farrell’s
obligations under this Agreement without the necessity of showing any actual damage or the
inadequacy of monetary damages. Any such equitable remedy shall not constitute the sole and
exclusive remedy for any such Default, and the Company shall be entitled to pursue any other
remedies at law or in equity. In the event of a Default by Farrell, the Company shall be entitled
to (a) recover from Farrell its costs, including reasonable attorneys’ fees, incurred in enforcing
its rights under this Agreement and (b) cease making payments to Farrell under paragraph 2 of the
Separation Agreement without invalidating any portion of the Separation Agreement or this
Agreement.

(b) Any court proceeding to enforce this Agreement may be commenced by either party in the
Berkshire Superior Court, Pittsfield, Commonwealth of Massachusetts. The parties hereto submit to
the exclusive jurisdiction of such court and waive any objection which they may have to the pursuit
of any such proceeding in such court.

7. Entire Agreement. This Agreement, together with the Separation Agreement,
constitutes the entire agreement between the parties relating to the subject matter hereof and
supersedes any and all previous agreements, oral and written, between the parties with respect to
the subject matter hereof.

8. Non-Waiver. The failure by a party in one or more instances to insist upon
performance of any of the terms, covenants or conditions of this Agreement, or to exercise any
rights or privileges conferred in this Agreement, or the seek enforcement of any of the terms,
covenants or conditions of this Agreement following any breach of any of the terms, covenants,
conditions, rights or privileges, shall non constitute, nor be deemed to constitute, a waiver of
any of the terms, covenants or conditions of this Agreement, but the same shall continue and remain
in full force and effect as if no such failure or forbearance had occurred. No waiver of the
terms,
covenants or conditions of this Agreement shall be effective unless it is in writing and signed by
an authorized representative of the waiving party.

 

4

 

9. Applicable Law. This Agreement shall be governed and controlled as to validity,
enforcement, interpretation, construction, effect and in all other respects by the internal laws of
the Commonwealth of Massachusetts applicable to contracts made and wholly to be performed in the
Commonwealth.

10. Binding Effect; Benefit. This Agreement shall inure to the benefit of and be
binding upon the parties hereto and their respective successors, assigns, heirs and personal
representatives. Nothing in this Agreement, express or implied, is intended to confer on any
person other than the parties hereto and their respective successors, assigns, heirs and personal
representatives any rights, remedies, obligations or liabilities under or by reason of this
Agreement.

11. Amendments. This Agreement shall not be modified or amended except pursuant to an
instrument in writing executed and delivered on behalf of each of the parties hereto.

12. Severability. Any term or provision of this Agreement that is invalid or
unenforceable in any situation in any jurisdiction shall not affect the validity or enforceability
of the remaining terms and provisions hereof or the validity or enforceability of the offending
term or provision in any other situation or in any other jurisdiction. If the final judgment of a
court of competent jurisdiction declares that any term or provision hereof is invalid or
unenforceable, the parties hereto agree that the court making the determination of invalidity or
unenforceability shall have the power to reduce the scope, duration, or area of the term or
provision, to delete specific words or phrases, or to replace any invalid or unenforceable term or
provision with a term or provision that is valid and enforceable and that comes closest to
expressing the intention of the invalid or unenforceable term or provision, and this Agreement
shall be enforceable as so modified after the expiration of the time within which the judgment may
be appealed.

13. Counterparts. This Agreement may be executed in any number of counterparts, each
of which shall be deemed an original and all of which together shall constitute one and the same
instrument.

IN WITNESS WHEREOF, the parties hereto have executed this Agreement as a sealed instrument as
of the date first above written.

	 	 	 	 	 
	 	/s/ David B. Farrell
 	 
	 	DAVID B. FARRELL 	 
	 	 	 
	 	BERKSHIRE HILLS BANCORP, INC.,

 	 
	 	By:  	/s/ Linda A. Johnston
 	 
	 	 	Its Senior Vice President — Human Resources 	 

 

5

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