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Reddish Knob to Wild Oak: Chestnut & Grindstone Ridge Shuttle



13.3 mile 21.4 kilometer point to point
55% Singletrack


Ascent: 975' 297 m
Descent: -3,733' -1,138 m
High: 4,384' 1,336 m
Low: 1,627' 496 m


Avg Grade: 7% (4°)
Max Grade: 20% (12°)


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Trail shared by Mark Hoyle

A great way to experience Wild Oak on Chestnut and Grindstone ridges without the Camp Todd climb.

Mark Hoyle

Electric Mountain Bikes Unknown

Features -none-


Flowy, fast, great for the downhill riding, but rugged enough to keep you honest. This route mixes short gravel road, doubletrack, and epic singletrack all in one fun experience. It is a great way to ride this trail without being super fit and riding TWOT!

Need to Know

If taking the bail out on Skidmore, be sure to know how much water is in North River as it can be VERY fast and deep.

This routes uses a part of the big Wild Oak N.R.T. (716) ... you can combine this with a ride on Lookout to get some of the best portions of this great ride!


If you like going downhill fast and still getting in some climbing, this is a great trail for you! It is a wilder, less-refined version of the Reddish Knob Ride down Timber & Wolf ridge with some beautiful New England-like riding on the doubletrack using Forest Road 85 and FS Road 427 (Bald Mountain Road).

The route is really easy to follow... You park one car at the lower Wild Oak parking lot, same as used by Lookout, and either ride up or set up a shuttle and drive up to the top of Reddish Knob. If riding, you can do the traditional ride up the paved road, or you can ride UP Wolf Ridge (378) and Timber Ridge Trail (431).This has some steep hike-a-bike sections but is doable.

Once on Reddish Knob, take in the views, then start downhill. Leave the top and about 400 yards past where the trail comes in on the right for Wold / Timber, you'll turn left onto Forest Road 85. Then after a fun, fast gravel downhill, turn left onto gated FS 427 at mile 1.5. This is a really fun ride out to Little Bald Knob... lots of water bars to jump and easy climbing.

At about mile 6.0, in the big clearing on Little Bald Knob, pick up the Wild Oak N.R.T. (716) on Chestnut Ridge and go-go-go! The only intersection is at mile 10.5. Turn left to go up and over Grindstone Ridge, or bail out turning right on Skidmore Fork Trail.

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We need help with the following missing trail information:

Family Friendly, ADA Accessible, Dogs Allowed, Features, Electic Mountain Bikes Allowed, History & Background


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Aug 11, 2019
Matt Stroebel
Some epic singletrack mixed with scary loose rocky sections and gnarly climbs with lots of fallen trees. 13.3mi — 2h 40m

Trail Ratings

  4.0 from 5 votes


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in Virginia


59 Views Last Month
2,327 Since Jun 9, 2017



View from Reddish Knob. The rock to the right of the bike is the top of Timber Ridge Trail.
Oct 2, 2016 near Franklin, WV
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
quick shot of reddish knob and the rocky section on Timber Ridge Trail.
Dec 17, 2014 near Franklin, WV
Winter ride on the Wild Oak Trail.
Dec 27, 2016 near Bridgew…, VA


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