The southeastern corner of Vermont is characterized by the gentle foothills of the Green Mountains as they descend in wave upon wave down to the Connecticut River Valley. Starting in 1724, this was the first part of Vermont to be founded—late compared to the rest of New England.

The first permanent settlement in the state was at Fort Dummer, an outpost for protecting the fertile Connecticut River Valley from Native American raiders from the north. The fort grew steadily from a vibrant trading post to a solid base of manufacturing, eventually becoming the city of Brattleboro.

In the mid-19th century, it became known as a therapeutic center, famed for a “water cure” that drew some of the country’s most prominent citizens for plunges in its ice-cold springs. Later, it became the “organ capital of the country” for its Estey Organ Company.

North of Brattleboro, smaller dairying communities sprang up in the surrounding hills, including the cheese-making center of Grafton. West of town, the so-called Molly Stark Trail, otherwise known as Route 9, climbs into the Greens.

Getting to the Brattleboro Area

To get to Brattleboro from Boston (115 mi., 2 hrs. 15 min.), take Route 2 west to Greenfield, then I-91 north to exit 1. From Hartford (85 mi., 1 hr. 30 min.) and Springfield (60 mi., 1 hr.), Brattleboro is a straight shot north up I-91 to exit 1. From Manchester, New Hampshire (80 mi., 1 hr. 40 min.), take I-93 and I-89 to exit 5, then head west along Route 9 to the Vermont border.

Amtrak (800/872-7245, www.amtrak.com) trains stop at Brattleboro Train Station (10 Vernon Rd.) once daily. Buses with Greyhound Bus Lines (800/642-3133, www.greyhound.com) run to Brattleboro from Boston and New York City, stopping at the Vermont Transit Terminal (Rtes. 5 & 9, 802/254-6066).