+1 for the Berkshires -  were you to include some time here in the 'shire, 
there's a bunch of us who could point you towards / ride with you on a lot 
of amazing back roads / dirt roads / logging roads, as well as some great 
climbing, and descending  (and there's some flattish - river path roads too)

Also, for those of you in New York City or on the MetroNorth commuter line, 
the last stop, Wassaic, is on a rail trail that is a nice 35 miles from 
Great Barrington and a lot of wonderful riding.  A great day trip (long 
though).

Ron

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