Follow in the footsteps of Daniel Boone along this 93.8-mile National Scenic Byway that traces one of America’s most storied pioneer routes through the heart of Kentucky’s Appalachian country.

Beginning at Cumberland Gap—the legendary mountain pass where Boone blazed his trail in 1775—the highway winds northward through a tapestry of rugged mountain terrain, pastoral valleys, and charming small towns. You’ll pass through the Daniel Boone National Forest, where ancient hardwoods blanket rolling ridges and roadside overlooks reveal sweeping vistas of the Cumberland Mountains.

Stop at Cumberland Gap National Historical Park to explore the famous natural passage, then continue through Pineville and Barbourville, where historic courthouses and locally-owned eateries offer authentic Appalachian hospitality. Near the northern terminus in Berea, discover Kentucky’s folk arts capital, home to renowned craftspeople and the celebrated Berea College.

The route showcases stunning fall foliage from mid-October through early November, though spring wildflowers and summer’s lush greenery offer equally compelling drives. Plan three to four hours for the drive itself, or a full day to explore historic sites, hiking trails, and artisan shops along the way.

This is Kentucky at its most genuine—where history, natural beauty, and mountain culture converge.

Explore Nearby

• Lorain West Breakwater Light(aka: Lorain Harbor Light) — Lighthouse in Ohio
• Findley State Park — State Park in Ohio
• Vermilion Light — Lighthouse in Ohio
• Tinker’s Creek State Park — State Park in Ohio
• Fry Family Park — Dark Sky Site in Ohio