Lenox, Massachusetts

Like many of the charming towns that line this part of the Berkshires, Lenox is at its best when combining two worlds - the gorgeous pastoral quietness of the East Coast countryside with the exciting, always-novel artistic legacy of the Berkshires. Lenox has it all. A participant in the annual Tanglewood Music Festival, as well as home to one of the country's best summer stock companies, and within easy reach of cultural events like Jacob's Pillow, Lenox has all the benefits of city life - from fine dining to great nightlife - without ever sacrificing its historical charm. The Red Lion Inn, a slightly pricey but very much worth it hotel and restaurant, is the must-try place in this town, although other options include the Bistrot Zinc and the Church Street Cafe. While public transport can be difficult in this part of the Berkshires - often involving several bus changes - those with a car will find getting around easy. Good nearby schools include Berkshire Country Day and the artier Bard at Simon's Rock.