The gateway to Vermont for travelers driving north on Interstate 91, Brattleboro is a cultural and artistic community 120 mi/195 km southeast of Burlington. It has lots of ecominded and social-activist residents, plus a food co-op and nice small shops. It has a lovely reservoir, known as the Retreat Meadows, where the West River empties into the Connecticut River (canoes are available for rent). The Estey Organ Museum displays the world's only collection of Estey reed organs from the Victorian era. It is located in one of the six massive buildings where the organs were made for almost 100 years.

Downtown Brattleboro has experienced a revival with the restoration of the town's old movie house and the Latchis Hotel, an art-deco beauty. The chamber of commerce has outlined a walking tour of historic sites downtown. There are a number of interesting shops nearby, including Vermont Artisan Designs and several excellent bookstores. The town has a lively arts scene, which it celebrates the first Friday of every month with Gallery Walk, and the Strolling of the Heifers Parade and Festival in early June has become a major attraction.

More established, but also more weather-dependent, is the annual two-day ski-jumping tournament at Harris Hill Ski Jump. It's usually held in February and reliably draws a contingent of talented Austrians, Slovakians or Ukrainians warming up for the FIS World Championships.

North of Brattleboro is Dummerston, where author Rudyard Kipling lived in the 1890s and wrote Captains Courageous and The Jungle Book. His home is located on 55 acres/25 hectares of meadows and forest and is available for weeklong stays through the British Landmark Trust, which bought and restored the property in 1992.

Just west of Brattleboro is Marlboro, home in June and July to the Marlboro Music Festival, a renowned chamber-music series. Southwest of Marlboro, in Jacksonville, is the North River Winery, housed at a farm that dates to the mid-1800s. Tours and tastings are available.

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