The Wilderness Road

The Wilderness Road lies at the convergence of Virginia, Tennessee and Kentucky, along the Cumberland Gap, and provides a natural passageway through the Appalachians. It used to be a seasonal thoroughfare for migratory animals and a native footpath, but by 1775 Daniel Boone was commissioned to blaze the Wilderness Trail through the mountains, and twenty years later this same route was rebuilt as a wagon road which would lead almost 300,000 settlers from the eastern states into what is now known as Kentucky.

Exploring the Wilderness Trail

The spectacular Cumberland Gap Highway Tunnel now beckons visitors through the rugged mountains into Kentucky, and sections of the original trail have been returned to a footpath. Even within the Cumberland Gap National Historical Park itself, you’ll find a section of the restored Wilderness Trail, and it may give you a rather eerie feeling, an almost mystical experience, to be walking in the footsteps of those pioneers of long ago! This particular hiking trail will lead you to Gap Cave, which would’ve been a familiar landmark to the early trail blazers. A guided tour of the cave itself (conducted by lantern light) will include glimpses of magnificent stalactites and stalagmites, Civil War-era graffiti, and a variety of wildlife (including bats, cave crickets, and salamanders).

Cumberland Gap National Historical Park

While in Cumberland Gap National Historical Park, be sure to check out the awesome view of the Gap and the Wilderness Road that’s available from Pinnacle Lookout. And you may also decide to visit the Hensley Settlement, an abandoned mountain settlement that is now managed by the National Parks Service (it will give you a feel for the lifestyle of the early, self-sufficient mountain settlements of Appalachia). The Wilderness Road Campground (along US 58, in Virginia) offers tent and pull-in camping.

Continuing Along the Wilderness Road

After exploring Cumberland Gap National Historical Park, you’ll use routes US 25E and KY 229 (which are now designated as a National Scenic Byway - the Wilderness Road Heritage Highway) to trace the original route of the pioneers through the rural countryside. Heading north, you’ll pass Middlesboro (“the city built inside a meteorite crater”) and Pineville (which was originally known as Cumberland Ford and evolved around the construction of a tollgate at The Narrows on the Wilderness Road) before arriving at Pine Mountain State Resort Park (Kentucky’s first state park, opened in 1924), where you’ll find spectacular vistas of the Cumberland Mountains and several intriguing hiking trails for your exploration.

Daniel Boone, Country Music, and More

Continuing northwest along the old Wilderness Road route, other interesting places you can visit include Daniel Boone Memorial Park (where a monument marks the only point where all three major pioneer trails, the Warrior’s Path, Boone’s Trace, and the Wilderness Road, converge), Camp Wildcat Civil War Battlefield (site of the first Union victory of the Civil War in Kentucky), Levi Jackson Wilderness Road State Park (where there are sections of the original Boone’s Trace and Wilderness Road - and a working gristmill), Whitley’s Station (which was a stopping point for pioneers, the site of the earliest horse track in Kentucky, and is now the location of the William Whitley House), Renfro Valley (where you can visit the Kentucky Music Hall of Fame & Museum and attend the “Barn Dance”, its renowned, long-lasting country music show), Berea (designated as the “Folk Arts and Crafts Capital of Kentucky”), and Fort Boonesborough (where you’ll be given a guided tour of the reconstructed wilderness fort that was founded by Daniel Boone back in 1775).

An Adventure Trek Near the I-75

The Wilderness Road route is a very informative and interesting adventure trek - and it’s located just east of the I-75 and just south of Lexington, so it’s very accessible.

For More Information:

Southern & Eastern Kentucky Tourism Development Association SEKTDA), 2292 South Highway 27, Somerset, KY 42501; web site: www.tourseky.com; phone: 877-8687-7359.

Related Kentucky Travel Articles

• Berea
• Red River Gorge
• Cumberland Falls State Resort Park
• Sheltowee Trace National Recreation Trail