Wilderness Road Trail is one of the most popular trails in Cumberland Gap National Historical Park. The Wilderness Road refers to the trail widened by Daniel Boone into a road. The road led settlers into Kentucky through the Cumberland Road. Although it has been called a road since 1775, it was usually more of a footpath over rough and rocky terrain. Robert Kincaid wrote an excellent and definitive book on the Wilderness Road.
In Cumberland Gap National Historical Park, more people walk on the Wilderness Road Trail than any other trail. The trail in the park runs from the Daniel Boone Parking area in the town of Cumberland Gap to the Thomas Walker Parking Area, a distance of approximately two miles.
There are three reasons the trail is so popular. First, it goes through the historic Cumberland Gap. There is a sign that tells you when you have arrived at the Gap and I tell everyone it is the obligatory selfie spot. The second reason the trail is so popular is because it is the easiest trail in the park. The third reason the trail is so popular is that it takes you to the Tri-State Peak trail. By climbing an additional 0.6 miles, you get to the place where Tennessee, Virginia, and Kentucky all meet.
Tom and I have walked the trail numerous times. On Sunday afternoons, Tom leads a Gap hike, which follows along part of the Wilderness Road trail. When our friends were visiting, we took them on a hike to the gap. A couple of weeks before they came, we hiked to the gap from the Daniel Boone Parking area. Hiking the Wilderness Road trail from the Daniel Boone parking area is shorter, but also steeper. Coming at the trail from the Thomas Walker parking area means the trail is wider with a more gradual incline.
It is pretty cool to hike the Wilderness Road Trail to the gap. As you are trudging along, you can think about being one of those first pioneers heading into Kentucky, afraid of Indian attack at any moment. You are carrying or have on a packhorse everything you own. Those first settlers must have heaved a sigh of relief when they reached the gap, even though they still had hundreds of miles to go before reaching the place they would settle.
Wilderness Road extends beyond the gap to Boonesborough, Kentucky. It also continues into Virginia. There is a bike trail that goes along US 58 in Virginia and follows the historic trail. Tom and I intend to ride it, but it does not connect to the national park, so we will have to load up the tandem in order to get to the trailhead. The trail goes through the Wilderness Road State Park.