Itineraries
Historic Sites
The site of a military outpost built in 1724, Brattleboro is the Byway’s most southerly Waypoint and now one of its largest urban centers. Its cosmopolitan atmosphere was established in the 19th century by a mineral springs resort that attracted travelers to a promised “water cure” and 
continues today thanks to the School for International Training, whose students and teachers come from many countries. A vibrant downtown that celebrates the performing and visual arts is focused along a Main Street that follows the curve of the adjacent Connecticut River.
Brattleboro is the Waypoint community for an area that includes the towns of Vernon, Guilford, Dummerston, and Putney, VT, and Hinsdale, Chesterfield and Westmoreland, NH. There is a Waypoint Welcome Center in the Strolling of the Heifers/River Garden on Main Street in Brattleboro. The designated Byway routes in the Brattleboro area are Routes 5 and 142 in Vermont and Route 63 in New Hampshire.
Nature & Scenery
The exposed rock and forested slopes of New Hampshire’s Mt. Wantastiquet create a dramatic backdrop for Brattleboro’s downtown, and includes trails of the Mt. Wantastiquet State Forest. The Connecticut is joined to the south of town on the New Hampshire side by the Ashuelot River and to the north on the Vermont side by the West River, where a large cove, known as the Retreat Meadows, is a gathering place for migratory waterfowl on the Connecticut River flyway.
History and Culture
The downtown is an historic district with plenty of restaurants, bookstores and events. At the cultural heart of Brattleboro – itself a regional cultural center – is the Brattleboro Museum & Art Center www.brattleboromuseum.org/ Brattleboro’s Union Station was among the last generation of major railroad passenger stations built in Vermont. It was constructed of stone in 1915-1916 for the Central Vermont and Boston and Maine Railroads. The station is now home to the Brattleboro Museum & Art Center.
Fort Dummer was the earliest European outpost north of the present Massachusetts border, built in 1724 during a period when armed conflict with Native Americans persisted all over New England. The fort was abandoned, but settlers returned in the late 1700s to establish a community along the Whetstone Brook. It blossomed with the growth of industries like the Estey Organ Company, the world’s largest manufacturer of reed organs, which in 1880 employed more than 500 and made more than a quarter million organs before pianos eclipsed their popularity.
Two historic steel bridges from the early 20th century span the Connecticut River between Brattleboro’s downtown and Hinsdale. Covered bridges in the Brattleboro region of Vermont include the Creamery Bridge over Whetstone Brook, the Green River Bridge in Guilford over the river of that name, and Vermont’s longest covered bridge, the West Dummerston Bridge over the West River. New Hampshire covered bridges in the area include four in Swanzey that span the Ashuelot River: the Slate Bridge, the West Swanzey Bridge, the Sawyer’s Crossing Bridge, and the Carleton Bridge. Two more covered bridges over the Ashuelot are in Winchester – the Ashuelot Bridge and the Coombs Bridge.
Recreation
The Vernon Dam on the Connecticut River creates a pool or low-current area that extends north beyond the mouth of the West River. The West is popular with canoeists and kayakers. The region is home to a growing number of hiking trails. Mt. Wantastiquet itself is a popular hiking destination. State parks in the area include: