Mountain Biking
River Road, Arlington (9-13 miles): This is a country ride on almost level terrain, paralleling the Batten Kill as it flows from Arlington to New York State. Ride west from Arlington on Rt. 313, turning left and crossing the river at 0.6 miles to continue west (right) along River Road. Easy riding past farms reaching West Arlington (covered bridge) at 4.4 miles. Turn around here and return by the same route, or continue on River Road a few more miles.
Red Mountain Loop, Alrington (17 miles): A challenging ride of moderate length. Some paved sections. Ride west from Arlington to West Arlington (as described above), cross the bridge, turn right, then left on Sandgate Road at 5 miles. At first climbing, then over more gradual terrain (good views of Mt. Equinox), continue to Southeast Corner Rd. Turn right, beginning a 2.5 mile uphill. Moderate at first, the last two miles on this rough jeep road are fairly tough going. The descent to Route 7A is long and at times steep. On Rt. 7A turn right and return to Arlington.
Shaftsbury back-road loops: For some easy gravel road riding, drive north from Bennington on Route 7A to South Shaftsbury or beyond. Various loops on gentle terrain are possible in the area east of Route 7A – from South Shaftsbury north to Arlington. See the map. The Up and Downhill (bike shop) in Bennington has some detailed maps for some commonly done routes here.
Woodford area: From Bennington drive east on Route 9 to the Prospect Mountain Ski Area, drive south on Forest Service Rd. #273 and park. There is a very extensive network of rideable trails and roads in this area. Inquire at Mountain Bike Peddler for detailed information about the various local rides. The southern Green Mountain National Forest with its many old roads is a goldmine for the mountain biker.
Road Biking
Bennington Covered Bridges (10 miles): From the Bennington Battle Monument, start out on Fairview Street, turning right on Silk Road. This will bring you to (surprise) the Silk Road covered bridge and Route 67A. Turn left on 67A and ride for a short distance to Murphy Road. Turn left, crossing the Paper Mill Bridge. Continue another mile or so before coming to the Henry Bridge. After crossing this, turn right on Route 67A, and ride back to Bennington on Northside Dr. and Benmont Ave. to Main Street. Pick up Elm Street one block south of Main, climb up to Monument Ave., turn right, pass the Old First Church and continue to the monument and your starting point.
Bennington Historic Loop (15 miles) : A longer variation of the above, this ride starts at the monument, crosses the three covered bridges, but loops through North Bennington as well. After crossing the Henry Bridge, turn right on Route 67A, then left on Park Street Extension, making the climb up to Mechanic St. (some gravel). Turn right and after about a mile, turn right again, on Mattison Rd. Turn onto Rice Lane (after a mile) which becomes Houghton Lane. Good views from the Route 7 overpass. South on East Road back to town. Right on County St and back to Benmont Ave.
Bennington-Hoosick Falls Loop (25 miles): Most of this ride is on minor roads away from traffic and with good views of farming country. From Bennington, follow Bank Street to Walloomsac Road (or take Route 9 west) until it merges with Route 9. After crossing the New York line, continue on County Road 100 and Bresse Hollow Road to County Road 95 (Petersburg Junction Rd.) which takes you north into Hoosick Falls. From here continue north on Route 22 to County Road 102. Head right (east) and stay on this to Bayer Road, followed by Ore Bed Road which brings you back to North Bennington. Take Route 67A back to Bennington.
Bennington-Pownall Loop (35 miles): A hilly loop on beautiful rural highways south through Pownal, west into New York state and north to North Bennington. Be sure to take food and drink as there are very few changes to buy refreshments. From the east end of County Rd., ride south out of Bennington, crossing Route 9 and reaching South Stream Rd. which merges with Barber Pond Road. It swings around to the west and meets US Rt.7. The route resumes its westward course on North Pownall Road, just a bit to the north. Continue westward on Route 346 to Green Road in New York state. Take Green Rd. north to County Road 100 (Breese Hollow Road), crossing NY Route 7 onto Ore Bed Rd. which brings you into North Bennington. Continue east on Route 67A back to Bennington
Hiking Trails
Bald Mountain Trail, Bennington: Excellent views of Bennington, Massachusetts, and New York State. The trail begins near the water tanks on Bolles Brook Road. Turn left (north) off Route 9 at the Woodford Town Hall, about 4 miles east of Bennington. It is 1.9 miles to the summit of Bald Mountain, elevation 2,857’. Return by same route or, if you have arranged for transportation, continue on the Bald Mountain Trail directly back down to Bennington, a distance of 3.5 miles for a total of 5.4 miles.
Harmon Hill 2,320’ Bennington Area: Good views of the Bennington area. Drive about 5 miles east from Bennington on Route 9 to the Long Trail/Appalachian Trail crossing and park. Hike south on the LT/AT for 1.7 miles to reach the top. The first mile or so is quite steep.
George Aiken Wilderness: Located south of Route 9 in Woodford town, this 5,000 acre wilderness with no designated trails is quite accessible. From Woodford, 8 miles east of Bennington, drive south on Forest Road #74 to pick up the 4-mile long Yaw Brook Trail (it runs south to F.R. # 73) which skirts the east side of the wilderness. A high, (over 2,000’) and generally wet area, the wilderness offers excellent opportunities to fish and observe beaver and other wildlife.
Visit or call the Forest Service for more information and detailed maps on the wilderness areas in the Green Mt. National Forest. Technically the areas are not wilderness, but the policy is one of the non-intervention, allowing the designated areas to revert to a more primitive state.