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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.
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.
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