Winding 156 miles through the rugged beauty of Tennessee’s Upper Cumberland region, this National Scenic Byway traces a path rich in pioneer heritage and Appalachian splendor. Beginning at the Cumberland River in Celina and culminating near the legendary Cumberland Gap National Historical Park, this route follows the footsteps of Daniel Boone and countless settlers who pushed westward through these ancient mountains.

The journey reveals dramatic limestone bluffs, rolling farmland, and dense hardwood forests that blaze with color each autumn. Stop at Dale Hollow Lake for world-class fishing, explore the charming town squares of Livingston and Tazewell, and discover hidden waterfalls tucked into mossy hollows. History comes alive at Civil War sites, preserved homesteads, and the iconic Cumberland Gap—the natural passage that opened the American frontier.

Small-town hospitality awaits in communities where time moves slower and front-porch conversations still matter. Local eateries serve up authentic Southern cooking, while antique shops and craft galleries showcase Appalachian artistry.

Best Time to Visit: October offers peak fall foliage, though spring wildflowers and summer’s lush greenery each hold their own appeal.

Allow: A full day for the drive, or two days to truly explore the historic sites, hiking trails, and scenic overlooks along the way.

Explore Nearby

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• Paint Rock Creek Covered Bridge — Covered Bridge in Tennessee
• Obed Wild and Scenic River — Dark Sky Site in Tennessee