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             EXHIBIT 5   OPINION OF MULDOON MURPHY AND FAUCETTE LLP








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                        [MULDOON MURPHY & FAUCETTE LLP]



                                February 28, 2001




Board of Directors
Berkshire Hills Bancorp
24 North Street
Pittsfield, Massachusetts 01201

      Re:   Berkshire Hills Bancorp, Inc. 2001 Stock-Based Incentive Plan
            Registration Statement on Form S-8 for Offer and Sale of
            1,074,326 Shares of Common Stock

Ladies and Gentlemen:

      We have been  requested  by  Berkshire  Hills  Bancorp,  Inc.,  a Delaware
corporation  (the  "Company"),  to issue a legal opinion in connection  with the
registration  (the  "Registration")  of 1,074,326 shares of the Company's Common
Stock,  $.01 par value (the  "Shares"),  on Form S-8 under the Securities Act of
1933.  The  Registration  covers  767,376  Shares  that may be  issued  upon the
exercise  of  stock  options  and  306,950  Shares  that may be  distributed  as
restricted stock awards under the Berkshire Hills Bancorp, Inc. 2001 Stock-Based
Incentive Plan (the "Plan").

      We have made such  legal and  factual  examinations  and  inquiries  as we
deemed advisable for the purpose of rendering this opinion.  In our examination,
we have  assumed and have not verified (i) the  genuineness  of all  signatures,
(ii) the authenticity of all documents  submitted to us as originals,  (iii) the
conformity  with the  originals of all documents  supplied to us as copies,  and
(iv) the accuracy and completeness of all corporate records and documents and of
all certificates and statements of fact, in each case given or made available to
us by the Company or its subsidiary, Berkshire Bank.

      Based on the  foregoing and limited in all respects to Delaware law, it is
our  opinion  that the  Shares  reserved  for  issuance  under the Plan are duly
authorized  and,  upon  payment  for and  issuance  of the  Shares in the manner
described in the Plan, will be, legally issued, fully paid and nonassessable.

      The following  provisions of the Certificate of  Incorporation  may not be
given effect by a court applying Delaware law, but in our opinion the failure to
give  effect to such  provisions  will



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Board of Directors
February 28, 2001
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not  affect  the  duly  authorized, validly issued, fully paid and nonassessable
status of the Common Stock:

      (a)   Subsections  C.3 and C.6 of Article FOURTH which grant the Board the
            authority to construe and apply the  provisions  of that Article and
            subsection  C.4 of Article  FOURTH,  to the extent  that  subsection
            obligates  any  person to  provide  the Board the  information  such
            subsection  authorizes  the  Board to  demand,  in each  case to the
            extent,  if any, that a court  applying  Delaware law were to impose
            equitable limitations upon such authority; and

      (b)   Article NINTH which  authorizes  the Board to consider the effect of
            any offer to  acquire  the  Company  on  constituencies  other  than
            stockholders in evaluating any such offer.

      This opinion is rendered to you solely for your benefit in connection with
the  issuance of the Shares as described  above.  This opinion may not be relied
upon by any other person or for any other  purpose,  and it should not be quoted
in whole or in part or otherwise referred to or be furnished to any governmental
agency (other than the Securities and Exchange Commission in connection with the
aforementioned  Registration  Statement  on Form S-8 in which  this  opinion  is
contained) or any other person or entity  without the prior  written  consent of
this firm.

      We note that,  although certain portions of the registration  statement on
Form S-8 (the  financial  statements  and schedule)  have been included  therein
(through  incorporation  by reference) on the authority of "experts"  within the
meaning of the Securities Act, we are not experts with respect to any portion of
the  Registration   Statement,   including  without   limitation  the  financial
statements  or schedules or the other  financial  information  or data  included
therein.

      We hereby  consent  to the  filing of this  opinion  as an  exhibit to the
Company's  Registration  Statement on Form S-8, and we consent to the use of the
name of our firm under the heading "Interests of Named Experts and Counsel."



                                          Very truly yours,

                                          /s/ Muldoon Murphy & Faucette LLP

                                          MULDOON MURPHY & FAUCETTE LLP


