Historic Wilderness Road
Walk in the footsteps of Daniel Boone through the Cumberland Gap pass.
The Trail That Opened Kentucky
The Wilderness Road is more than a trail — it's a path through American history. Blazed by Daniel Boone and his team of axmen in 1775, this route through the Cumberland Gap opened the western frontier to settlement. Today, the historic road is preserved within Cumberland Gap National Historical Park near Middlesboro, offering hikers a chance to connect with Kentucky's pioneer heritage amid stunning Appalachian scenery.
Pioneer Heritage
Blazed by Daniel Boone in 1775, the Wilderness Road opened Kentucky to settlement through the Cumberland Gap — right on Middlesboro's doorstep.
Hiking Trails
The historic route winds through Cumberland Gap National Historical Park with trails for all skill levels.
Scenic Overlooks
The Pinnacle Overlook offers ridgetop views of three states and the Middlesboro meteor crater.
Interpretive Signs
Historical markers along the corridor tell the story of Boone's expedition and pioneer life.
Plan Your Hike
Location
Cumberland Gap National Historical Park, accessible from Middlesboro via US-25E
Difficulty
Ranges from gentle forest paths to rugged ridgeline trails
Bring sturdy boots, water, a trail map, and a camera. Best foliage views in October.
Gear up for the Wilderness Road
Hand-picked hiking, camping and fishing gear, plus trail books, for Middlesboro adventures.
Stay near the Wilderness Road
Compare hotels, motels and cabins around Middlesboro and Cumberland Gap on Expedia.