The Wild Oak Trail begins and ends in Stokesville, VA in a parking lot off FR 95. It has been designated a National Recreation Trail since 1979. This trail is commonly backpacked in either direction as a 2-3 day trip but can be completed in 1 day by trail runners.
There is a section of the trail that passes next to the Ramsey's Draft Wilderness Area between Spring House Ridge and Dividing Ridge. The trail ascends Shenandoah Mountain into the upper reaches of the Potomac River Watershed and teeters along the edge of the James River Watershed to the South.
Popular mountain bike segments of this trail include Lookout Mountain, Chestnut Ridge, Grindstone, Hankey Mountain, and Horse Trough Hollow. It has a mix of ridgeline riding, a contour-built reroute, a fast descent, and a lot of rock.
Horse Trough Hollow is often climbed to reach the Chestnut Ridge descent. This loop is known as "Camp Todd-Chestnut" which brings riders into the backcountry past Todd Lake onto a long gravel climb up Leading Ridge Road onto FR 95 where riders pickup TWOT on the right for a 2 mile climb up "Horse Trough Hollow" shortly after passing Camp Todd. The climb up Camp Todd/Horse Trough Hollow is steep, strenuous, off-camber, rocky and exposed in some spots. The climb ends along a cliff line providing views of Ramsey's Draft Wilderness Area and Eliot's Knob. Little Bald Knob is at the top where there's a well marked intersection. Stay right at the intersection for a 7 mile ridge ride that will blow your mind. This section of TWOT is known as the Chestnut segment. Fast, fun, flowy in sections with a few drops and spicy turns thrown in there to keep it exciting.
The Lookout Mountain Loop
is a featured ride in and of itself and is a recommended section for those riders willing to find the flowy line amongst a sea of rocks. (The flow is there, we promise).
Just off the Lookout Mountain section of TWOT, there is a great overlook as the trail approaches the North River, and a suspension bridge that crosses the river near the end.
The SVBC has done considerable amounts of trail rehabilitation on Lookout Mountain, Chestnut Ridge, and Horse Trough Hollow