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Good advice from Woof! on taking the back roads, tho' it would force you to go through Holyoke...*shudder*...and you could pick up I-91 that way, unless there's another way I haven't heard of.
Amherst has a great sense of community and though it can seem pretentious (lots of professors and college students discussing particle physics and Baudelaire over an espresso and biscotti), it's well worth it. Its population is quite diverse, laid-back and the shops and restaurants in town are interesting, though often expensive, as is the housing. The cultural activities, including those for kids, are many and varied.
You might want to try North Amherst or Leverett, for a more rural atmosphere, but a short hop to Amherst. Northampton is more cosmopolitan, and living in Florence would get you out of the city atmosphere (there's also Look Park and its great bike path) but is still clost to "Noho". The town of Williamsburg is much the same, but more "quaint" and has an excellent school system. The other good thing about living on that side of the river is that you can get on I-91 to Springfield very quickly, as opposed to getting caught on Rte. 9 for an hour or more, if you lived in Amherst!
Other nice, family-oriented towns I would recommend are: Hatfield, Whately, Shutesbury, South Deerfield and Sunderland (great school system in the latter 2). The latter are great for commuting, since you can quickly get to both Amherst or Northampton (15-20 mins.), and pick up I-91 in 5 minutes or so.
I'm going to include Greenfield, Ashfield, Shelburne Falls and Conway on here, though they're quite a haul from Springfield. Greenfield is not as community-oriented as the other towns, but there are some nice neighborhoods and housing is much less expensive. Conway & Ashfield are adorable and Shelburne has a great town center with nice shops, the famous "Bridge of Flowers" and other amenities. All these are at least 45 min. from Springfield, though.
You should take a ride out here again and cruise though some of the towns with your family. There are so many diverse types of "atmosphere", I'm sure you'll find something you love!
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