Why don't you check out Western MA, esp. Northampton aka noho.com?. It's known as the Five College area, with Smith, UMASS, Amherst, Hampshire and Mt. Holyoke in it or nearby, so it has a lot of stuff going on all of the time. For music stuff, just click here and you'll see over 100 listings of upcoming events in the area.
The whole area is full of wonderful campsites, B&B's, eclectic food venues, wonderful shops, although it has become a bit yuppiefied and expensive, and all kinds of neat historical places to visit, including Old Deerfield. When we used to go there, they had an album of songs which included one about an old man who lived there whose philosophy about life was to "have a coffee and doughnut for breakfast" memorialised in one of those songs.
As well, Noho itself has the famous Academy of Music where one can see movies, plus Noho also has an old art deco movie theatre, the Calvin, and an arts "cinema" with two screens.
Ah, I see Smith College has told it a bit more succinctly than I: Northampton: Smith's Home Town. They have a beautiful botanical gardens, btw.
There's lots more, if you are interested, please let me know.:-)