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Wild Oak N.R.T. (716)

 4.3 (3)

Big Mountain Backcountry Singletrack Loop not commonly ridden in its entirety.

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4,329' 1,319 m


1,607' 490 m


5,624' 1,714 m


5,575' 1,699 m



Avg Grade (5°)


Max Grade (36°)

Dogs Off-leash

E-Bikes Unknown

Bikes not permitted in Wilderness Areas. Trail passes through Ramsey's Draft Wilderness Area on the Southwestern most corner.


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


Shared By:

Shenandoah Bicycle

Trail Ratings

  4.3 from 3 votes


  4.3 from 3 votes
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in Virginia


28 Views Last Month
4,385 Since Jan 2, 2015


Photos video of Lookout Mountain Trail.
Dec 14, 2014 near Bridgew…, VA
Per the description, if you can time your ride to reach the overlook before sunset, you'll be greeted with a fantastic photo op!
Nov 2, 2020 near Bridgew…, VA
Optional lines on newly rerouted trail
Sep 19, 2013 near Bridgew…, VA
Snow covered Little Bald Knob before dropping into Chestnut Trail
Jan 6, 2020 near Bridgew…, VA
Getting a little spicy on the Wild Oak trail.
Jun 12, 2017 near Bridgew…, VA
Adventureseen video of Camp Todd and Chestnut
Jan 27, 2015 near Bridgew…, VA


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Nov 21, 2018
Paul Wolfram
11mi — 1h 45m
Mar 8, 2017
Marc-andré Perrault
Mar 15, 2015
Karen Talley Mead