If you enjoy biking to establishments, it's worth it to actively think about dirt roads and rail trails in your search -- dirt roads cut car speeds to safe levels, and rail trails let you avoid cars almost entirely. Both make biking miles better.
It's also almost evenly centered between NYC and Boston if you want to do weekend city adventures. You'll probably still need a car but if you live in the center of town you won't use it except for longer trips.
That is how I became aware of western Mass, actually. FWIW education is a major driver for us since we have 3 young kids. My thinking waffles a bit because there's a list of criteria in my head, like being walkable, bikeable, having a downtown area, in addition to the more major concerns we have as a family around education, local economy, and affordability. I appreciate the reply!