This 25 mile "loop" (part of the northern section is cut off by wilderness) might be one of the best rides in George Washington and Jefferson National Forests. Starting from Horse Trough Hollow, a brutal climb to the top of the 4,300 foot Little Bald Knob awaits. Expect pretty technical climbing at high grades. Your reward is one of the best descents in the East. Rooty, narrow, boostable, and fast, the Chestnut Ridge descent packs a true wilderness vibe and as much descent as the far more popular Timber Ridge Trail into even less distance. Just make sure to keep you eyes on the trail at all times. This is rocky, loose Virginia riding at its finest.
After crossing the North River, a technical 10 mile climb of 1,800 feet is in front of you as a price for 3,000 feet of descent. At the top of Hankey Mountain, soak up the views of the Shenandoah Valley below. Afterwards, enjoy a 1,000 foot descent before starting the blisteringly steep climb up Bald Ridge. The grade will average at more than 20%, so make sure your derailleur shifts into your granny gear before starting.
At the top of the ridge, you will be confronted by the fact that a mile or two of the trail enters wilderness, making it impossible to complete by bike. Either head back down the way you came or walk with your bike on your back through the wilderness portion. If you choose the later option, you can hop on your bike and ride one last loose descent of 1,200 feet before you reach your car. Enjoy!
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