Named for the jaw-dropping Great Falls of the Housatonic River, this tiny community is surprisingly eclectic. Home to legendary Music Mountain, the oldest continuing summer chamber music festival in the country, as well as the progressive Isabella Freedman Jewish Retreat Center, Falls Village looks like a town that time forgot. Listed on the National Register of Historic Places, Falls Village boasts easy access to the Appalachian Trail and a well-preserved Main Street with 18th and 19th-century houses in a variety of architectural styles. The village center also features quirky Toymakers Cafe (which is popular with weekend motorcyclists).