I used to live in Northampton myself (and Amherst; and Easthampton).Wonderful area! You must go to Atkins' Farms at the base of Mt. Monadnock in South Amherst. Lovely scenery surrounds a fabulous natural foods/fresh fruit shop.
For entertainment, well the Iron Horse would be the thing. Good food, too.
(sigh) I miss the Happy Valley.