Super cute town, lots of great shops, restaurants, museums, home of Smith College and the Botanic Garden of Smith College, which we have heard is lovely. We will be staying in Northampton.
This offering to say that there is a lot of great hiking in Western MA. Northampton, North Adams, Lee, Westfield, Southwick and Springfield all have options in addition to the provided forest in CT.
The annual FreshGrass Festival, an outdoor music fest, is also the same weekend in North Adams. You may catch a few guests on Sunday if you opt in!