Backroads of the Cumberlands


Backroads of the Cumberlands

Seven breathtakingly scenic routes make up Spearhead’s Backroads of the Cumberlands. Designed for street legal vehicles and bicycles, these routes wind their way through some of Southwest Virginia’s most picturesque paved and gravel backroads. Roll the windows down, feel the warmth of the sun on your face, and you will be transported back in time to the days of Sunday drives with the ones you love most!

Around the Clinch

Beginning in Gate City, Virginia, this route takes you along the Clinch River as it winds its way into Tennessee. Along the way, your sights will include waterfalls, swinging bridges, and open, rolling farmland dotted with cattle, horses, sheep, and more! Be sure to plan a visit to the Daniel Boone Wilderness Trail Interpretive Center and the Natural Tunnel State Park as you pass through Duffield, VA.


Beginning and ending in the town of Big Stone Gap (the namesake and setting of the 2014 movie starring Ashley Judd and Whoopi Goldberg), your journey will lead you past the highly photographed Powell Valley Overlook as you approach the City of Norton, eventually making your way to the Big Cherry Reservoir. Here you will find a network of dirt and gravel roads that lead around High Knob, where you will find the High Knob Fire Tower Lookout. This is a good time to stretch your legs for the short walk to the tower, where you will be greeted with magnificent long-range views of the Southwest Virginia mountains. Complete the loop back to Big Stone Gap, where you can visit the Harry W Meador Coal Museum or attend the Official Outdoor Drama of Virginia.

Wilderness Road

Explore America’s First Gateway to the West - the path that Daniel Boone blazed in the late 1700’s - as you embark on this historic route. You can still envision the herds of buffalo and elk that populated this fertile valley as your drive through the backroads of Lee County. Visit the Wilderness Road State Park, Cumberland Gap National Park, or plan an overnight stay at a local Airbnb so you can hike to the Sand Cave or the White Rocks – both of which are geographical wonders.


If you are looking for gravel and dirt roads, this is the route for you! Mainly located on US forest roads, you will have many opportunities for short, rewarding hikes on this route. Little Stony Falls welcomes you at the end of a short stroll down a well-groomed trail, cascading from under a small footbridge into a crystal-clear pool. Visit Flag Rock to take your picture with the Woodbooger, the area’s version of “Bigfoot”. You can also take a short walk to the High Knob Tower, a phenomenal overlook that will take your breath away! Finish your day of exploring in the City of Norton, or town of Coeburn or Dungannon.

Big Moccasin

Beginning in the town of Weber City or Nickelsville, this route takes you along Copper Creek and Big Moccasin Creek. Along the way, you’ll find small “Mom & Pop” restaurants, Creation Kingdom Zoo, and a short hike to the Mendota Fire Tower, which will offer excellent bird watching as well as nearly 360-degree views from atop the Clinch Mountain. Don’t forget to plan your evening at the Carter Fold! You can then return to one of several B&B’s or Airbnb’s and wrap up the night by sitting on the front porch and watching the stars emerge in the night sky.

*Riders should be cautious around low water bridges during heavy rains, as they may be impassable


Beginning in the town of Pennington Gap, this route leads you through farmland and forests on its way to Big Stone Gap. Visit the pristine mountaintop Keokee Lake where you take a waterside stroll or possibly even kayak or check out Caves Springs swimming area and walking trails! Take the time to stop at the Daniel Boone Wilderness Road Interpretive Center for an awe-inspiring look back in time. Finish your day back in Pennington Gap, where you will find both Airbnb’s and campgrounds to rest your head.


Named “Blackwater” by early hunters due to the levels of salt in the streams, this area was once a popular hunting ground for Native Americans who hunted buffalo, deer, and elk. Often overlooked by the outside world, this route will take you along ancient trade routes and hunting paths on its way to Sneedville, TN. You can learn about the Melungeon people and outlaw moonshiner Mahala Mullins who was catchable but not fetchable. Stop by the new Axe Handle Distillery on your way for some legal spirits.