This ride’s general location is Pittsfield. Scenery is densely wooded. This ride is not for the timid; experts can add 9 miles and a 900′ climb by starting at the village green in Pittsfield. This ride is a combination of rarely used dirt roads and jeep trails impassable by four-wheel-drive vehicles. A one-mile rocky descent in what appears to be a washout will have you yearning for a full-suspension bike. The bone-jarring downhill is followed by the ride’s highlight, a shady climb on a winding, single-lane dirt road with a steep drop-off to Fletcher Brook on the left. If you seek solitude, you will like this ride. You will definitely need to be in good shape for this ride. The terrain is very challenging with several short, technical climbs, one long climb along Fletcher Brook, and a one-mile descent that you will most likely walk.


Activity Type Mountain Biking
Nearest Town Pittsfield
Length  9.5 total miles
Elevation Gain 900 feet
Trail Type Loop
Skill Level Advanced


Trailhead: From Pittsfield, drive south on VT 100 for 2 miles. Turn left onto South Hill Road and climb for 2.3 miles to the top. Park anywhere along the road at the T-intersection.

Latitude/Longitude: 43.739864,-72.78859

Directions: Begin by turning right and riding south on the gravel road (South Hill Road), immediately passing South Hill Cemetery on your left. After 1 mile, begin looking for a narrow jeep trail on the left. Take the jeep trail, which climbs steeply at first, but becomes more level and easier to ride. Stay with the main vein, ignoring two lesser roads that veer off to the left. Pass a shack on your left and at 2.6 miles come to a fork. Take the washed-out trail/road to the left and begin descending – this is the rocky descent that you will most likely walk. At times you might wonder what you are doing here, but push on, it will soon be over. At 3.5 miles, just after a short, rideable climb, you will come to a dirt road with a brown house on the right. Stay right, keeping the house on you right and arrive at a T-intersection. Stay right and continue descending to an intersection of several roads.This is the low point of the loop (in elevation, not mood). Take the sharp right dirt road, keeping Fletcher Brook on your left.

Climb steadily on this road, passing several right-hand options. Stay left at the Road Closed sign. Fletcher Brook should still be on you left. Pass a shack on your right and take the left fork. Pass another shack on your right and take the right, uphill fork. This trails brings you to a T-intersection with the “Jones” house directly opposite you. Turn right onto the gravel road.

At 7.8 miles pass a narrow road on you right marked with VAST trail signs for Prior Dam Road and Barnard. Shortly after that, pass Brown Road on your right. After a fast descent you will pass, on your right, the jeep trail that took you into the woods at the beginning of the ride. From there it is 1 mile back to the start for a total of 9.5 challenging miles.



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