Brattleboro Itineraries

A| 14.6 Miles; approx. 35 minutes

Start: Brattleboro Byway Waypoint Center Strolling of the Heifers – River Garden, 157 Main Street, Brattleboro, VT)

  • Head north on Main Street, following signs for VT-30 north to Newfane (as you exit the downtown area, turn left on Park Place and right onto Linden Street).
  • Continue along VT-30, West River Road, until West Dummerston Covered Bridge.
  • Follow the sign for East-West Road, turning right through the covered bridge, then turn right onto East-West Road.
  • When East-West Road turns to the right, continue straight ahead onto Schoolhouse Road.
  • Turn left onto US-5 North, and continue for approximately 3 miles.

Finish: Putney (Putney Town Hall, 127 Main Street, Putney, Vermont)

Attractions and Detours along the way: Brattleboro downtown (musical events, art exhibitions, cultural festivals, Brattleboro Museum and Art Center, as well as a large number of historic buildings); view of Mt. Wantastiquet across Retreat Meadows; West Dummerston Covered Bridge (Vermont’s longest covered bridge); Putney Village (home to many local artisans and artists); Union Station; Creamery Covered Bridge (1.4 miles along VT-9 west of Brattleboro, on Guilford Street), Naulakha (Rudyard Kipling’s home); Molly Stark Byway along VT-9; Scott Farm

B| 10.4 miles; 20 minutes

Start: Putney (Putney Town Hall, 127 Main Street, Putney, Vermont)

  • Continue heading north on US-5 Main Street.

Finish: Westminster (Westminster Town Hall, 3651 US Route 5, Westminster, VT)

Attractions and Detours along the way: Westminster Village (where Vermont declared itself a free and independent state in 1777);  Westminster Old Cemetery

C| 17 miles; 35 minutes

Start: Westminster (Westminster Town Hall, 3651 US Route 5, Westminster, VT)

  • Continue heading north on US-5.
  • Take a slight right onto VT-123, then turn right to go under the railway bridge.
  • After crossing the Connecticut River, turn right onto NH-12. As NH-12 branches left, continue straight on NH-63. Crossing NH-9, continue on NH-63 south to Chesterfield.

Finish: Chesterfield (near Chesterfield Town Hall, 490 Route 63, Chesterfield, NH)

Attractions and Detours along the way: Park Hill Meeting House; Westmoreland Village; Spofford Lake; Chesterfield Village (including stunning views across the Connecticut River to the Green Mountains); Asbury Methodist Church; Chesterfield Gorge (about 3.4 miles east of NH-9)

D| 14 miles; 25 minutes

Start: Chesterfield (near Chesterfield Town Hall, 490 Route 63, Chesterfield, NH)

  • Continue heading south of NH-63.
  • When you reach Hinsdale, turn right to continue on NH-63 south (also NH-119 west), following signs for Brattleboro.
  • After crossing the Connecticut River, turn right onto Main Street in Brattleboro.

Finish: Brattleboro Byway Waypoint Center (157 Main Street, Brattleboro, VT)

Attractions and Detours along the way: Hinsdale Main Street; Bear Mountain; Pisgah State Park; Ashuelot Covered Bridge (about 3.6 miles east on NH-119 on Gunn Mountain Road); Wantastiquet Mountain State Forest; Black Gum Swamp (Vernon)

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