I was walking down the northern hill on South Main the other day, and I realized that it must have been re-routed at some point.
If you look at a map of Bratt (and there's one 2 clicks away, on this site's main page), once the road hits the hill (going north), it turns west a bit, then upon arriving at the monument shop, turns further, only to veer back. Knowing that roads are expensive, and it makes more sense, in general, to keep them straight, I got to thinking. I found a map of Brattleboro as it lies today, and South Main, before the second turn going down the hill, is pointing straight at Main St.
Surely this road must've at some point been moved, but why? What was removed to make room for this change? What other changes did it allow?