Great Barrington is one of my least favorite places on Earth. The people there are bougie and divorced from reality even by Birkenstock Belt/Tofu Curtain standards, and the Bard satellite campus for formerly-swottish teenagers there, where I went for three semesters before transferring to my beloved ZooMass Slamherst, is a wretched hive of scum and villainy. The rest of the area is lovely.
Yeah, I like edgier places myself, and thus I live on the "wrong" side of the tracks in Hudson, right next to two section 8 houses. Went to Bard eh? Dan and I go there often for concerts, and sometimes lectures. Lots of cute guys. Met some of them too. 
But I get what you are saying. To spend a fortune, to go to that type of school, strikes me as a bit dubious right of the box. Was in your hood to visit Emily Dickenson's house. She is my first cousin about 5 times removed or something. All that genius being generated on that tiny desk of hers, in that tiny bedroom that she rarely left. Amazing.
You know, I'd be happy to grab drinks (hot, alcoholic, both, or neither) or lunch somewhere in the Berkshires some time if you would.
