Bicycling Southern Itinerary


South Loop

Easy loop starting from Brattleboro

Distance: 11 miles

Time: Approximately 1 hour

Parking: There are a variety of parking lots in Brattleboro’s downtown. Go to  * How may we help you *  Parking information

Bicycle rentals: Available in Brattleboro

Start: at Indian Point Park approximately 3.9 miles south from the Brattleboro Waypoint Center (157 Main Street) on VT-142.  The park will be on the left.

  • Turn right onto Newton Road after approximately 4.9 miles.
  • After 1.6 miles, turn right at the T-intersection onto Pond Road.
  • After 1.7 miles, turn left on VT-142, traveling north back to Indian Point Park.

Finish: Indian Point Park.


South Loop Extension

Moderate loop starting from Brattleboro

Distance: 49.1 miles

Parking: see easy loop information. Also consider starting the loop in one of the other villages or downtown areas along the route.

Bicycle rentals: available in Brattleboro and Putney

Note: This route can easily be made into a shorter loop by using one of the other bridges across the Connecticut River. See the map for the location of river crossings.

Start:  at the end of the easy loop at the Brattleboro Waypoint Center (157 Main Street), continue heading north on US-5/Main Street and continue on US-5 as it becomes Putney Road.

  • At the traffic circle (2.3 miles into the ride), continue straight onto US-5 north and follow it through the villages of Putney and Westminster to Bellows Falls (20.1 miles).
  • In Bellows Falls, take a slight right onto Westminster Street and continue onto Rockingham Street.
  • After 0.8 miles, turn right onto the bridge and cross the Connecticut River into New Hampshire.
  • After crossing the bridge, take NH-12 south towards Walpole.
  • After 10.1 miles, take the slight right onto NH-63 south towards Westmoreland and Chesterfield. (Do not follow NH-12 around to the left towards Keene, NH.)
  • After 2.3 miles, turn right onto River Road and continue as it becomes Main Street.
  • After 8.1 miles, turn right onto Brook Street for 500 feet, then turn onto Cross Road and continue as it becomes Ferry Road.
  • When you reach the main road (after 0.8 miles), turn right onto NH-9 west for 1.9 miles.

Finish: After crossing the Connecticut River again into Vermont, take the 3rd exit on the traffic circle onto US-5 south/Putney Road. Follow US-5 south as it becomes Park Place, Linden Street and Main Street, to return to your starting point after 2.3 miles.

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