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I'm not from Brattleboro, but I am seriously considering relocating there, from New York City.
Yes, it is an artsy town. There is always something to do in terms of the arts. Galleries, concerts, folk dancing, all sorts of stuff.
On the first Friday evening of every month, there is Gallery Walk. I attended one in the rain and there were lots of people and lots of music. The next day was the Strolling of the Heiffers, so maybe there were more people there than usually.
There is a train that goes through town. It goes to Penn Station in New York City and also, I think, to Essex Junction, VT. I don't think it goes very frequently, though, maybe only once a day.
There are several sporting goods stores and there is an Outing Club. I can't contribute anything about schools, etc., but I do know that there is lots of indoor and outdoor recreation available.
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