EXHIBIT A NON-SOLICITATION AND NON-COMPETITION AGREEMENT

May 3, 2011

Michael J. Oleksak

15 Patriot Lane

Feeding Hills, MA 01030

Dear Mike:

For the reasons that we have discussed, Berkshire Hills Bancorp, Inc. and Berkshire Bank (collectively, the "Company") and you have reached a mutual decision to terminate your employment. The Company desires to resolve any and all issues relating to the conclusion of your employment 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.  The terms of your separation are intended to recognize your service to the Company and to protect and promote the Company’s legitimate interests.  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 May 13, 2011 (the “Termination Date”).  You shall be paid your earned salary through the Termination Date, less legally required withholdings.

2.           Although you are not otherwise entitled to it, in consideration of your acceptance of this Letter Agreement and in recognition of your service, the Company shall provide you with severance pay of $350,000 (“Severance Pay”), less legally required withholdings.  Your Severance Pay shall be paid in two (2) equal installments of $175,000 each, as follows: (i) on the Company’s next regularly scheduled pay date following the Termination Date, or eight days after the date on which you execute this Letter Agreement and return it to the Company without revocation, whichever is later; and (ii) on the Company’s first regularly scheduled pay date in April 2012.  In the event of your death prior to the payment of the full amount of your Severance Pay, the right to receive any remaining installments of your Severance Payment shall inure to and for the benefit of your estate and any personal representative appointed in connection with the settlement thereof.  You agree that under the terms of one or more certain “Berkshire Hills Bancorp, Inc. 2001 Stock Based Incentive Plan Restricted Stock Award Agreement(s)” and “Berkshire Hills Bancorp, Inc. 2003 Equity Compensation Plan Restricted Stock Award Agreement(s)” you may have entered into with the Company, you hereby forfeit your unvested Stock Awards, as defined in such agreements, as of the Termination Date and all of your rights to any unvested stock 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.

3.           The Company also agrees to provide you with group health and dental insurance coverage, if applicable, through May 13, 2011.  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 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 and Berkshire Hills Bancorp Inc.'s organization or through which they conduct business.

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 any 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.

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 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.

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.  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.

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.

BERKSHIRE BANK

By: /s/ Michael P. Daly                                                      

      Michael P. Daly

      President and CEO

The undersigned understands and agrees completely to the

foregoing as of May 5, 2011

/s/ Michael J. Oleksak                                                                           

Michael J. Oleksak

Witness: /s/ Wm. Gordon Prescott                                                                           

  Wm. Gordon Prescott

This Non-Solicitation and Non-Competition Agreement (this “Agreement”) dated April _____, 2011 and effective as of May 13, 2011, between BERKSHIRE BANK, a Massachusetts banking corporation with a principal place of business located in Pittsfield, Massachusetts and MICHAEL J. OLEKSAK of Feeding Hills, Massachusetts (“Oleksak”).

The Company (defined for purposes of this Agreement to mean and include Berkshire Bank, together with its parent corporation Berkshire Hills Bancorp, Inc. and primary affiliate 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 Oleksak 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 Oleksak Separation Pay in the gross amount of $350,000, less customary payroll taxes and deductions and payable as set forth in paragraph 2. of the Separation Agreement; and

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

The duration of this Agreement is eighteen (18) months from the Termination Date set forth in the Separation Agreement; provided, however, that notwithstanding anything else herein to the contrary Oleksak’s obligations under Section 3 of this Agreement shall continue in perpetuity; and

Oleksak 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. Oleksak 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)           Oleksak hereby agrees that, beginning on May 13, 2011 and for a period of eighteen (18) months thereafter - until November 13, 2012 – (the “Non-Competition Period”), Oleksak 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 any counties where Berkshire maintains a Branch Office (a “Competitor Employer”), without prior approval from Berkshire’s President and CEO, Michael P. Daly (“Daly”).  Notwithstanding anything else to the contrary herein, such approval is hereby given for Oleksak to accept the position of Executive Vice President of Lending at Peoples Bank in Holyoke, Massachusetts, and Oleksak’s employment in such position shall not be considered a Prohibited Activity.  No other approval to engage in any other Prohibited Activities for or on behalf of any Competitor Employer is given, made or inferred by this by this Agreement.

(b)           Oleksak 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 Oleksak for the purpose of requesting that Oleksak engage in Prohibited Activities with a Competitor Employer during the Non-Competition Period, Oleksak may request that Daly waive the provisions of Section 1(a) of this Agreement.  Daly shall consider Oleksak’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 his absolute and sole discretion, Daly decides to grant the waiver request, the waiver shall not become effective until Oleksak and the Company, acting at Daly’s direction, shall have entered into a written modification of this Agreement, signed by both parties.

2.           Non-Solicitation.  Oleksak hereby agrees that, beginning on May 13, 2011 and for a period of eighteen (18) months thereafter - until November 13, 2012 - Oleksak 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)           Knowingly solicit 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 Oleksak’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 Oleksak’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 Oleksak may accept employment with a Company client or customer or prospect that is not a Competitor Employer; or

3.           Protection and Non-Disclosure of Confidential Information.  Oleksak hereby agrees and acknowledges that his employment with the Company has created a continuing relationship of confidence and trust between Oleksak and the Company with respect to Confidential Information.  Oleksak 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 Oleksak 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, Oleksak has first provided to the Company as much advance notice as practicable of any such compelled disclosure, and further that Oleksak 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 Oleksak 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 Oleksak 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 Oleksak’s obligations under this Agreement regarding Confidential Information or otherwise.

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

5.           Defaults.  Oleksak shall be deemed to be in default of his obligations under this Agreement (a “Default”), if Oleksak shall have breached his obligations under Section 1 hereof and such breach shall continue for 15 days after the Company has given Oleksak notice of same.  Notwithstanding anything to the contrary contained in the foregoing sentence, Oleksak 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)           Oleksak 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 Oleksak’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 Oleksak, the Company shall be entitled to recover from Oleksak, among any other relief to which the Company may be duly entitled, (a) its costs, including reasonable attorneys’ fees, incurred in enforcing its rights under this Agreement and (b) any payments made to Oleksak 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.

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.

MICHAEL J. OLEKSAK

BERKSHIRE BANK,

By:                                                                

Print name: Michael P. Daly

Its: President and CEO