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            EXHIBIT 5   OPINION OF MULDOON MURPHY & FAUCETTE LLP




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                              May 30, 2003




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

      Re:   Issuance of 300,000 Shares of Common Stock Pursuant to the
            Berkshire Hills Bancorp, Inc. 2003 Equity Compensation Plan

Ladies and Gentlemen:

       We have been  requested  by  Berkshire  Hills  Bancorp,  Inc., a Delaware
corporation  (the  "Company"),  to provide  our opinion in  connection  with the
registration  (the  "Registration")  of 300,000  shares of the Company's  common
stock,  $.01 par value,  to be issued as awards of restricted  stock or upon the
exercise of stock options  granted or to be granted  under the  Berkshire  Hills
Bancorp,  Inc. 2003 Equity  Compensation Plan (the "Plan").  The Registration of
the shares is being effected on Form S-8 under the Securities Act of 1933.

       We have made such legal and factual examinations and inquiries as we have
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.

       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.  With respect to shares of Company  common stock  issuable  upon the
exercise of stock options  granted or to be granted under the Plan, upon payment
for and issuance of the common stock upon exercise of such stock  options,  such
shares of stock will be validly issued,  fully paid and nonassessable.  Further,
with respect to the awards of restricted  stock under the Plan, upon issuance of
such shares of stock in the manner  described in the Plan,  they will be validly
issued, fully paid and nonassessable.



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Board of Directors
Berkshire Hills Bancorp, Inc.
May 30, 2003
Page 2


       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 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 such section
            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.

       We note that, although certain portions of the Registration  Statement on
Form S-8 (the financial  statements and  schedules)  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"
therein.


                                    Very truly yours,



                                    /s/ MULDOON MURPHY & FAUCETTE LLP