Adding to @circuitrider … qualifier, no kid in attendance, but two have been through the recruiting process - one turned it down by a hair to attend Middlebury - hated it - transferred to and now attends Pomona - second one would choose it but likely won’t get through the pre-read, and if she does, I fear she’s one of those kids who might get that far and still face a risk of a rejection. Can’t waste that ED on anything but the safest bet.
With that out of the way, it is my distinct impression that the kids do make their way down to Main and use it as an alternative to campus food. We were blown away by the restaurant options there. Much more than you’d expect from a town like Middletown. And, as @circuitrider writes, Main Street is relatively charming.
Several blocks north of campus (if I have my compass set right) is a somewhat gritty neighborhood. No big deal, but it’s there.
If you want bucolic, it’s not in Middletown. At one point, I had two kids at Middlebury. One loved it and stayed; the other hated it and left, as I mentioned. The one who loved it loved campus life and appreciated the town. The one who hated it found campus life adequate (other than his coach), but could not stand the isolation and considered the town a detail that did not compensate for anything. What are you gonna do? [Dad shaking head at recalling all this].
Soooo, it depends on what you want. We found Middletown to be neither fish nor fowl. It’s not Mystic and it’s not Boston. It’s a small city or very large town. Main street is nice and it does offer some options for diversion, especially culinary. But it’s not enough in and of itself to compensate if you don’t like campus life. At lease in my opinion.
I think there’s a lot going on at Wesleyan … it always seemed like a really busy place when we visited. I think I would have liked to have attended there myself as an undergraduate if I’d known more about New England LACs.