Like most liberal/Dem leaning areas, much of the answer can be summarized in two words: social issues.
Plus, it's in Massachsuetts, one of the most (if not the most) liberal state in America.
No, but the Berkshires are a special kind of liberal; they voted for Coakley, when equally liberal areas voted for Brown.
I'd say that other posters are right when they describe it as a southern Vermont appendage.
Hmmm? No equally liberal areas came close to voting for Brown. The areas that voted for Brown were less Democratic (and far less liberal) suburbs and exurbs of Boston and smaller cities (Worcester, Springfield, Lowell, etc.). The swing is not completely uniform; generally, the less Democratic an area is, the greater the difference between its 2012 Presidential and its 2010 Senate vote. But the super-liberal areas, whether in the Berkshires or in Cambridge, were all solidly for Coakley. As were the rich liberals on the Route 2 corridor; Belmont, Arlington, Lexington, Concord, Lincoln, Acton, etc. all voted for Coakley, as did the comparable Newton and Brookline.
Coakley was also from the Berkshires (North Adams), so even if her performance had been unusually strong there (it wasn't), that shouldn't be a surprise.
If you're having trouble remembering, here you go:
http://www.boston.com/news/special/politics/2010/senate/results.html