Kent might be the quintessential New England town—nestled among hills that don’t so much roll as tumble alongside the Housatonic River. They surround a downtown that bustles with art galleries, outdoor sculptures, and eclectic shops. The foliage here is as good as it is anywhere, and the town makes it easy to appreciate it, with several outdoor parks and preserves to amble out among the leaves.

A few miles north up Route 7, you’d never know the Cornwall countryside—which includes Cornwall Bridge, Cornwall Plains, North Cornwall, West Cornwall, and East Cornwall—is a countrified version of the Hamptons, with homes here owned by Michael J. Fox, Whoopi Goldberg, Sam Waterston, and other big-name celebrities. Here, however, the idea is really to get away from it all. Old-time residents barely bat an eye when they see an actor at the general store or antiques shop, and that seems to be how everybody likes it.

Once upon a time, this area was heavily industrialized, taking advantage of the swift-flowing rivers and quantities of ore found in the hills to produce many manufactured metal goods. Those days are long gone, however. Now the unspoiled countryside seems tailor-made for leisurely afternoon drives or walks, with covered bridges and trickling streams flowing down from the hills.