Mama to DD1 2007, DS 2009, DD2 2012, What a Journey this parenting thing is...
We live a little farther north in S. Hadley but my mother lives in Hartford...There really aren't a lot of options that come to mind but maybe West Hartford or that area -- not really a lot in between that fits all those requirements. I would say it's more of a one or the other situation rather than being in between...
enfield is a large-ish city [25,000 people, i think?], i don't know how big or small you're looking for. but it has very easy access to 91, is really close to springfield, and has lots of local farms. they also have a great library and a couple parks, plus lots of little shops, a mall, several shopping centers [best buy, kohl's, home depot, etc], and is like 15 minutes from wal-mart. there are several awesome state forests within a half hour.
if you wanted smaller and less busy, look at suffield--still very close to everything i mentioned but quieter and a little more upscale. also somers is suffield-like, a little further from 91 and the big stores, a little closer to some of the farms and shops.
if you want rural, stafford springs is a half-hour from 91, 15-20 from 84, minutes from state forests, 5-30 minutes from farms, and 30-45 minutes from pretty much anything except a grocery store. also 45ish minutes from hartford and springfield. so, if you are a family who'll sacrifice closeness for countryness, it's a good place for it :)
good luck in your search!
edited to add: if you do move up this way, pm me :)
baby-dancin like crazy for #2 since july[darn that bf'ing! ]
We are in Windsor and it's a great town for tiny ones. The schools are not fantastic here but there is a lot to offer for littler kids. You could go to a free playgroup every day sponsored by the town. There are trails along the Farmington River to walk/ride a bike. We have a walkable center of town with restaurants, a town green that does free concerts all summer, and a weekly farmer's market. I live within walking distance of the center and take my stroller to the grocery store, post office, the train station ( a bit hit with little boys!), the library and the farmer's market. And the town is very diverse but solidly middle-class. We're 10 min north of Hartford and 30 min south of Springfield.
West Hartford is lovely, has great highway access, a Whole Foods and a Trader Joe's. There are lots of great activities for little ones and the school system is top notch.
Happy , delayed/selective vaxxing, WOHM to DD1 4/10 , DD2 8/12 and partner/wife for thirteen years to SAHD DH.