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!
Maybe. Two examples I've lived in or around are Chambersburg, Pennsylvania and Hattiesburg, Mississippi, with populations around 50k. Chambersburg is probably little bit more walkable because it's a little more dense, but neither are (in my opinion) comfortable for walking or biking outside of specific areas, and those specific areas don't have everything you need.
Unfortunately, there are relatively few places to live inside the dense part of town. The city is overly-zealous about maintaining historic districts and you'd better believe people get all up in arms about "changing the character of the neighborhood" every time a new development is proposed, even in non-historic and totally dilapidated areas. I've seen literally hundreds of millions of dollars worth of new housing and commercial projects be cancelled or indefinitely postponed due to this attitude just in the last 10 years.
While the city has a lot of potential, it's population has stagnated since the 1970s and the surrounding area has become a massive suburban sprawl. Many of the buildings downtown have been replaced with parking lots. Traffic is generally terrible, and the bus system has low coverage and poor frequencies.
Around 100 years ago, Portland was a thriving metropolis with electric trolleys going to every imaginable destination. All of those trolleys are gone now and their tracks have either been removed or awkwardly paved over.
Portland was once a vibrant inter-city train hub with hourly connections to the rest of Maine. The two primary stations, Union Station, and Grand Trunk Terminal, have been torn down. The current train hub, "Portland Transportation Center" is much further from the city center to make room for a large parking lot. It is about a 40 minute walk from what is considered the downtown area. 20 minutes by bus if your schedule happens to line up.
It's pretty disappointing how much better it once was. I'm doubtful that it will ever be as good as it was back then, but still hopeful. There are plans to move the train station back to where Union Station was. New routes to Lewiston and Rockland have been studied (although would apparently cost hundreds of millions to repair the tracks). The state has recently subsidized certain interstate train and bus routes to make them very affordable. And generally I think a lot of problems could be immediately solved by straightening out bus routes and increasing frequency, as well as obviously removing a lot of building-size restrictions and parking minimums.
What area were you referring to?
I did this. I have 100 restaurants, too many bars to count, music and theatre (three!) and festivals and arts within trivial distances. No car needed.