A|6.2 Miles; approx. 10 minutes
Start: Windsor Waypoint Center (3 Railroad Avenue, Windsor, VT)
- Head north on Railroad Avenue and turn left onto US-5, Main Street.
- Turn left onto Bridge Street at the second set of traffic lights towards Cornish.
- Travel through the covered bridge and turn left onto NH-12A north.
- Continue approximately 5.6 miles until you reach Plainfield Village.
Finish: Plainfield (Phillip Read Memorial Library, 1088 NH-12A, Plainfield, NH)
Attractions and Detours along the way: Windsor historic downtown (including the Common; Constitution House; American Precision Museum); Cornish-Windsor Covered Bridge; Saint-Gaudens National Historic Site; Blow Me Down Grange; Salmon P. Chase Birthplace; Lake Runnemede; Windsor Town Forest
B| 14.3 miles; 25 minutes
Start: Plainfield (Phillip Read Memorial Library, 1088 NH-12A, Plainfield, NH)
- Travel south on NH-12A.
- Turn left onto NH-12 east towards Claremont.
- Turn left onto North Street and continue to second traffic light, Waypoint Center on the right.
Finish: Claremont Waypoint Center (14 North Street, Claremont, NH)
Attractions and Detours along the way: Plainfield Village; Salmon P. Chase Birthplace; Claremont City Center (including Opera House Square Historic District; Mill District and bridges; view of Sugar River; Veterans Memorial in Broad Street Park); Cornish boat ramp
C| 30.7 miles; 60 minutes
Start: Claremont Waypoint Center (14 North Street, Claremont, NH)
- Continue east on North Street and turn right at the traffic light onto Broad Street, toward NH-12 south.
- Continue over the bridge and straight up the hill to Broad Street Park, staying right to go around traffic circle.
- Exit traffic circle onto NH-12 south/Pleasant Street, following signs for Charlestown.
- After approximately five miles, take the sharp right turn onto NH-12A, River Road.
- At the traffic light, turn left onto NH-12 towards Vermont.
- After crossing the Connecticut River, turn right at the traffic light onto US-5 north towards Windsor. Turn left onto VT-44A, then left at the stop sign onto VT-44 west.
- In Brownsville/West Windsor, turn right onto Brownsville-Hartland Road. Continue on the road until it reaches Hartland Four Corners.
- Turn right onto VT-12 south to get to Hartland Three Corners.
Finish: Hartland Three Corners (near Hartland Town Hall, 1 Quechee Road, Hartland, VT)
Attractions and Detours along the way: North Charlestown Historic District; Ascutney Village; Mt. Ascutney State Park; Brownsville Village; Sport Trails of the Ascutney Basin; Sugar River Rails-To-Trails; Ashley Ferry boat launch; Wilgus State Park; Weathersfield Bow on US-5; old quarry accessible from the Brownsville Hiking Trail on Mt Ascutney; Cady Mausoleum; Sheddsville Cemetery; Best and Bowers Covered Bridges
D| 27.9 miles; 50 minutes
Start: Hartland Three Corners (near Hartland Town Hall, 1 Quechee Road, Hartland, VT)
- Take Quechee Road north from the crossroads. Stay on the road until you reach US-4.
- Turn right onto US-4. Turn right onto VA Cutoff Road and then immediately turn right again.
- When the road ends, turn right onto US-5. Follow US-5 south through North Hartland and Hartland Three Corners to Windsor.
- Turn left onto Railroad Avenue to return to the Welcome Center.
Finish: Windsor Waypoint Center (3 Railroad Avenue, Windsor, VT)
Attractions and Detours along the way: Hartland Three Corners Village; North Hartland Village;
Willard Twin Covered Bridge on Mill Street
Connecticut River Heritage Trail
Greater Claremont Chamber of Commerce
Greater Lebanon Chamber of Commerce
Hartland Historical Society
Historic Windsor Walking Tour
Plainfield Historic Building Tour
Old Constitution House State Historic Site
Saint-Gaudens National Historic Site
Sport Trails of the Ascutney Basin
Sugar River Recreational Rail Trail
Upper Valley Trails Alliance
Woodstock Vermont Area Chamber of Commerce
Upper Valley Trails Alliance