Brattleboro is the largest town in southern Vermont, sitting where the West River meets the Connecticut. It has a reputation for progressive politics, independent-minded residents, and a lively arts scene that punches well above its size — the town has more artists and musicians per capita than almost anywhere in New England.
Main Street is lined with independent bookshops, galleries, ethnic restaurants, and food co-ops. The Brattleboro Museum and Art Center rotates quality contemporary exhibitions in the town's old Union Station. The farmers' market draws crowds on Saturdays throughout the growing season. The Latchis Hotel and Theatre, one of the few Art Deco buildings in Vermont, is both a cinema and one of the better hotels in town.
The town's unusual industrial history lives on in the Estey Organ Museum on Birge Street, housed in the factory complex of a company that once employed 700 people making reed organs for the world. In winter, the Harris Hill Ski Jump above town hosts competitions at an Olympic-calibre venue that has been in continuous use since 1922.
The literary connection is worth noting: Rudyard Kipling lived in the hills just north of town from 1892 to 1896, writing The Jungle Book in a house he called Naulakha. The Connecticut River forms the eastern edge of town, with trails along the bank and a well-preserved covered bridge a mile upstream.