Cumberland to Appalachia crosses Black Mountain at the highest point in Kentucky and is aptly named the Coalfield Black Snake run. Black Snakes are in abundance in this coal region and you're likely to catch a glimpse or so of snakes sunbathing on the road during the summer months.


Looking to the top of the mountain toward Virginia, you'll see a huge strip-mine. Once a mainstream way of life in the Appalachians, they're slowly disappearing. Into Kentucky, you will come down into the Lynch/Benham area which has a exhibition mine and the Kentucky Mine Museum. Both of these are great spots to stop and enjoy. In its hayday, Lynch had a population of over 10,000 and was the largest company owned coal camp in North America.

Approximately 129 miles

1. Start in Pennington Gap, VA

2. Take Rt. 421 N into KY

3. R on 38 in Harlan

4. R on 624 – Moonshiner’s Run

5. L on 606 at Keokee

6. Take 606/68 toward Appalachia

7. L on 23

8. L on 160 – Black Snake

9. Cross into KY on Route 160

10. L on 119 in Cumberland, KY

11. L on 421 at Baxter, KY

12. L on 421 to Pennington Gap, VA

To download a tank map for this route click the button below and unzip the zip file.


Mother's Place - Pennington Gap

1054 Big Hill Road   276-220-4169

Wolfe-Gilbert House - Dryden


Convenient Inn - Pennington Gap

131 Industrial Drive   276-546-5350

Wilderness Road Campground - Ewing

8051 Wilderness Road   276-445-3065


Rooster's Pub - Pennington Gap

41780 E Morgan Ave.   276-546-4190

Countryboy Cafe - Pennington Gap

41751 E Morgan Ave.   276-546-1645

Ruby's Steakhouse - Pennington Gap

131 Industrial Dr.   276-546-6900

El Centenario - Pennington Gap

205 River Bend Dr.   276-546-0044

Zona's Market - Keokee

13040 Rt. 606   276-565-1100


3. Lee Theatre
41676 W Morgan Ave.  Pennington Gap

5.  Southwest Virginia Museum State Park
10 W 1st St. N   Big Stone Gap

6. Trail of the Lonesome Pine Outdoor Drama 

518 Clinton Ave. E   Big Stone Gap


Created by VA General Assembly in 1993, we've been helping visitors and tourism-related businesses for nearly 25 years!


- Lodging, Dining, Shopping Info

- Outdoor Adventure Assistance

- Calendar of Regional Events

- Regional Attractions Info

-Outfitters & Guides Listings

- Travel Planning Assistance

  • Facebook Social Icon
  • Twitter Social Icon
  • Instagram Social Icon


3028 4th Avenue Market Square

PO Box 186, Saint Paul, VA 24283

© 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! offers road condition info.