Wilderness Road Trail


Wilderness Road Trail Facts

States: Virginia
Counties: Lee
Length: 8.5 miles
Trail end points: Old Wilderness Road/US 58 (TN-VA state line) and Daniel Boone Trail Rd./US 58 (near Ewing)
Trail surfaces: Crushed Stone
Trail category: Rail-Trail
ID: 6068510
Trail activites: Bike, Horseback Riding, Mountain Biking, Walking, Cross Country Skiing

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Wilderness Road Trail Description

History runs deep along the Wilderness Road Trail, which roughly follows a path carved by Daniel Boone in April 1775. The path later became a route on the Louisville and Nashville Railroad before finally being converted to a rail-trail that stretches from a national historic park to a state park.

At the western trailhead in Cumberland Gap National Historic Park, the Wilderness Road Trail connects to the 1.6-mile Boone Trail, which connects to a larger trail system that continues through the Cumberland Gap. Just beyond the trailhead in Cumberland Gap National Historic Park, you might catch a glimpse of impressive buffalo grazing in a privately owned, fenced area.

The first 2 miles run right next to US 58. Although this sounds unpleasant, you are separated from vehicles and there is something soothing about riding through forsythia toward forest and farmland. After this stretch, the trail backs into a quiet and much more scenic area behind a veil of trees, although the path still parallels US 58 until the trail's terminus just west of Ewing.

Once it retreats from the road, the trail meanders through nearly 7 miles of picturesque farmland, complete with bright white fences and grazing cattle. The route is dotted with quaint homes, barns and silos, and the impressive Cumberland Mountain serves as a backdrop to this idyllic landscape.

Wilderness Road State Park hosts reenactments and living history events throughout the year. The Joseph Martin House, located in the park and next to the trail, offers restrooms, a gift shop and local history exhibits. There is a user fee to enter the park.

Parking and Trail Access

To reach the westernmost trailhead in Cumberland Gap, head west from Bristol on US 58. Continue past the Heart of Appalachia Gazebo trailhead and paved parking lot on your right, which is about 4 miles west of Wilderness Road State Park. Continue west on US 58, and after another 2 miles, reach the trail's start point, where you'll find limited roadside parking.

If you're coming from the west on US 58, the trailhead is about 1 mile east of the intersection of US 58 and US 25E.

The easternmost trailhead is also right off of US 58 at a paved parking lot about 3 miles west of Ewing. If you're heading west on US 58 from Bristol, you'll see a sign stating that Cumberland Gap is 10 miles away. The parking area is on the north side of US 58.

Wilderness Road Trail Reviews

Road this today and unfortunately didn't make it past the part near the road that is way to Streep with the gravel. Ended up on my side with a slit in my shin and had to head back to the road and back to the car. Beautiful day but don't recommend this on a bike.

Rode the western end of the Wilderness Road Trail. It is mostly loose gravel. It is shared with horses so the hoof marks made the trail rougher. The trail runs parallel to the highway on this section. Not as scenic because of the highway noise. Also a bit hilly. Otherwise, a good trail to ride in the fall.

I have not experienced the same problems that previous reviewers have mentioned, except a few dogs that are easily outrun, or squirted with a little water.
the best parking is at Daniel Boone Parking lot in Cumberland Gap. The Daniel Boone has nice restrooms and water and also some maps and info.
From here you can head west over the gap into Kentucky, or Northeast into Virginia.

Heading west the trail is smooth and fast for cyclocross bikes and mt. bikes. road bikes might slide around too much on the fine gravel/dirt surface. you can ride side by side.
if you head northeast you will have a couple miles of single track, perfect for cyclocross and mt.biking fun with a couple stream crossings on wooden bridges. Not too technical, just fun. When the trail comes to the highway it runs parallel to the highway for a couple miles and the rocks get bigger. Mt. bikes will fly here and cyclocross riders need to pay attention to the surface. once you get to the gazebo parking lot the trail is super smooth again and flat and fast. from here it is 6.4 miles to the northern end (another good parking lot.) I have covered this portion in under 22 minutes. You could ride a road bike here but cyclocross bikes are better.

It is pretty fast with a smooth hard surface and a very shallow grade when not completely flat. (averages 0.3% uphill heading north) Look out for horse manure since the horse people just don't care about anyone else. They never heard of horse diapers.
that's my only complaint.


We rode our bikes on the multi-use trail a few weeks ago. I would have to say that we loved it and will be back when the weather gets cooler, still the ride was in the shade for most of the 8.3 miles that we rode. The trail is hard pack crusher mix gravel, and is soft in some places but no problem for a Mtn. bike or my beach cruiser with wide tires. It does get steeper and more difficult past Gibson Station about 4.5 miles from WRSP going to Cumberland Gap Park, which is as far as you can ride a bike. More geocaches are to be placed along the trail soon. Really a great trail for hiking or biking. Looks to be used mostly by horse riders, but we had the whole place to ourselves on a Sunday.

I'm pretty sure this was the most boring trail we have ever been on. My husband made the comment that after riding the Virginia Creeper Trail, it's hard to find another one that measures up. That being said, about 6 miles into this ride, the trail becomes rutted and like riding in wet sand. It was rough, rough riding that was not expected for a trail. It was so rutted out that we finally rode down and rode on the highway shoulder which was a much better ride, even on a mountain bike. After getting out of the rutted sand, we biked back onto the trail and continued back to the car. About 3-4 miles from the end, I was just taking my time doing some easy peddling, when out of the clear blue a Beagle Dog came barreling down off a bank after me, intent on having my ankle for lunch. Unbelievably I was able to outrun him until he gave up and went home. The ride from our home to the park was beyond sweet so it ended up being worth the trip specifically for the scenery. We would never make the trip back for the ride.

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