My grandparents have a vacation home in North Egremont and my parents are building a second home here (near Great Barrington in the Berkshires) so I have grown up knowing the area by car and by running, but haven't been exploring on bike yet. I'm hoping to get some biking in this summer if we have enough of a place to sleep in!
Mt. Greylock is the best climbing as far as I know, unfortunately it looks like the state will be paving the road to the top for the next two summers - do a search on Mt. Greylock hillclimb and you will come up with a bunch of road bike club/ touring sites. IMHO the roads in the berkshires are for the most part well maintained, smooth, not busy (except in the heart of touristy towns like Great Barrington, Stockbridge, Lee) but don't have much of a shoulder.
check out:
http://www.ridenoho.com http://www.berkshirecycling.org (not so sure if this site is still active)
here's a cue sheet and map for the 2005 greylock century:
http://www.berkshirecycling.org/rides/greylock_map.php Tyler Hamilton used to put on a charity century that ended on Mt. Greylock for the MS society, here is a link to their page that has some more cue sheets for various length rides:
http://www.nationalmssociety.org/...nt_detail.asp?e=6673 Have fun!
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