Lenox

The famed Tanglewood music festival has been a fixture in upscale Lenox for decades, and it's one of the reasons the town remains fiercely popular in summer. Booking a room here or in any of the nearby communities can set you back dearly during musical or theatrical events. Many of the town's most impressive homes are downtown; others you can only see by setting off on the curving back roads that thread the region. In the center of the village, a few blocks of shabby-chic Colonial buildings contain shops and eateries. Five miles south of Lenox is Lee, famous for its harder-than-average marble, quarried in 19th century for use in the cottages of the Vanderbilts and their ilk. Today the bustling downtown area has a mix of touristy and workaday shops and restaurants.