Follow in the footsteps of early pioneers through Virginia's westernmost county (Lee). Visit Wilderness Road State Park and Martin's Station to check out early handmade forts. Experience the pioneer trek through Cumberland Gap National Historical Park. Pinnacle Overlook offers a view of the Gap that opened settlement to the west.

Approximately 230 miles


1. Start west of Kingsport, TN on 11W

2. Take Rt. 70 N toward Kyles Ford

3. L on 58 at Jonesville toward

Cumberland Gap

4. R on 25E toward Middlesboro, KY

5. R on 119

6. R on 421 S to Pennington Gap

7. R on 58 A toward Jonesville

8. L on 70 S

9. L on 11W to Kingsport


Mother's Place - Pennington Gap

1054 Big Hill Road   276-546-2410

Wolfe-Gilbert House - Dryden

193 Wolfe Gilbert Rd   276-220-4169

Convenient Inn - Pennington Gap

131 Industrial Dr   276-546-5350

Wilderness Road Campground - Cumberland Gap

8051 Wilderness Rd   276-445-3065


Rooster's Pub - Pennington Gap

41780 E Morgan Ave   276-546-4190

Countryboy Café - Pennington Gap

41751 E Morgan Ave   276-546-1645

Ruby's Country Steak House - Pennington Gap

131 Industrial Rd   276-546-6900

Roger & Tiger's Deli - Pennington Gap

42149 E Morgan Ave   276-546-1307

El Centenario - Pennington Gap

930 E Morgan Ave   276-546-0044

Dutch Treat - Rose Hill

21332 Wilderness Rd   276-445-4024

A Better Burger - Jonesville

33739 Main St, Suite 102   276-346-6768

River Place on the Clinch - Kyles Ford, TN

2788 Hwy 70   877-483-7211


1. Cumberland Gap National Historic Park

91 Bartlett Park Road, Middlesboro, KY


2. Wilderness Road State Park

8051 Wilderness Rd Trail, Ewing, VA


3. Lee Theater

41676 W Morgan Ave, Pennington Gap, VA


4. Natural Tunnel State Park

1420 Natural Tunnel Parkway, Duffield, VA


5. SWVA Historic Museum State Park

10 W 1st St N, Big Stone Gap, VA


6. Trail of the Lonesome Pine Outdoor Drama

518 Clinton Ave. E, Big Stone Gap, VA

9. High Knob Tower & Recreation Area

Rt 233 W at the top of the mountain


Created by VA General Assembly in 1993, we've been helping visitors and tourism-related businesses for 27 years and growing!


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3028 4th Avenue Market Square

PO Box 186, Saint Paul, VA 24283

Map not to scale. Rings represent approximate

2 hour drive time.

© 2013-2020 Heart of Appalachia Tourism Authority

Our back roads are just that, rural working roads, traveled by residents, farmers, coal transport and a variety of visitors. Use caution while traveling and check road conditions before  riding unfamiliar routes.  Enjoy your ride!
511Virginia.org offers road condition info.