There are a few other towns in Dutchess similar to Dover Plains -- mainly the neighboring ones. Amenia and Pawling remind me of it, but Pawling is a bit bigger (or at least it seems that way). Millbrook is also fairly small and wide-open like Dover Plains but Millbrook is a lot more upscale of an area, just like Stanford and Clinton near it. Millerton, a few towns to the north, seems quite a bit like Dover Plains.
There are smallish villages along the Hudson/Route 9, but to be honest they don't really remind me of Dover Plains a lot. More traffic goes through them and you're closer to things to do.
