58A, the Alternate Route and Pennington Gap
While Daniel Boone’s Wilderness Trail, US Hwy 58 stretches from Scott County to the end of Lee County and Cumberland Gap, railroading took the alternate route. US 58 Alternate runs from Jonesville to Big Stone Gap and Pennington Gap is a pass for the tracks and once a depot. Coal mining nearby created the town.
Spearhead Trail’s Stone Mountain ATV Trail 
trail head is located at the welcome center campground at Leeman Field Park. Constructed in 1933, the world’s largest enclosed baseball field for 25 years, hosted the Pennington Gap Miners, a St. Louis Browns affiliate minor league. A greenway along the trout stocked river and an 18-hole disc golf course offer leisurely activity. Scheduled events such as dirt drag racing or tractor pull and entertainment at the restored 1946 Lee Theatre are accessible from Pennington’s ATV friendly streets.
Visit the Appalachian African-American Cultural Center for history, genealogy and a look at a once segregated one room school house full of memorabilia. Curators request you make an appointment for a guided tour.
Take pictures at one of the latest LOVEworks signs on the Virginia Tourism trail 
at the intersection of East Morgan Ave. and Bobcat Circle. In Pennington Gap, L represents the Lee Theatre marquee, O encircles the town’s logo Great Stone Face rock, V is a tobacco row, Lee County’s heritage crop, and E is within coal scattered railroad tracks.
On North 421, Great Stone Face Rock 
hangs precariously over the highway. Carved by nature centuries ago, the town’s logo is visible from the southern direction near the trestle. Train tracks tunnel through the bottom making way from mining communities of Bonny Blue, Kemmer Gem and the town of Saint Charles.
On Route 606, discover Lake Keokee 
at Mohawk Loop. Paddleboard, kayak and fish this hidden gem near Keokee, where the coal town commissary is listed on the National Register of Historic Places.Stop at the intersection of 606 and 421 and walk through the Stone Creek Outdoor Classroom and Park all located on Virginia’s Coal Heritage trail.
One mile East on 58A, since 1965, Patio Drive-In serves up the jumbo cheeseburger and homemade shakes among other menu choices . Always on the must-do list of returning Lee Countians remembering the long line of cruisers on Saturday nights.
58A East to Big Stone Gap follows the Appalachian Backroad’s Panther’s Breath trail. Pick a back road from their map or explore your own. Cave Springs Recreational Area near Dryden, part of George Washington & Jefferson National Forest, offers a shaded hike with an excellent view from above. A cave spring-fed swimming hole offers the real cool down and camping is available.
421 South to Dot, VA connects back to Hwy 58 and the Wilderness Road. Axe Handle Distillers offers tastings and a lesson on hand hewn logs from the company that brought them, Old Virginia Log Homes. 58 East to the top of Powell Mountain offers a beautiful view of Smokey Mountain foothills at the county line of Lee and Scott. Visit the Daniel Boone Wilderness Trail Interpretive Center in Duffield for a lesson on Boone’s trek as you’ve just crossed his path where he lost a son near Stickleyville.
Follow the Wilderness Road West all the way to Cumberland Gap National Park. Drive or hike the park or schedule a tour out to Hensley Settlement, high atop Cumberland Mountain where settlers lived until 1951 without the conveniences of modern day. On the mountain top east is White Rocks and Sand Cave, noticeable on the drive through Lee County near Ewing. These hiking destinations have a continuing link into the settlement. The high canopy offers plenty of blooming mountain laurel in summer, a waterfall at Sand Cave and views of Powell’s Valley. Gap Caverns near the state line, features scheduled underground tours of the cave once known as Cudjo’s, where soldiers took shelter and mined salt peter. Near Ewing, Wilderness Road State Park and the recreated Martin’s Fort feature re-enactments of indian raids and pioneer life and more information on Boone’s discovery West.
At Jonesville, visit the Lee County Veteran’s Memorial Wall at Cumberland Bowl Park. The county seat is the 1828 birthplace of Dr. Andrew Taylor Still, the founder of Osteopathic medicine. Lee County Historical and Genealogical Society sits just outside of town. Let your wanderLOVE go and see far Southwest Virginia. For more information, visit Heart of Appalachia Tourism or email info@townofpenningtonva.gov. We’ll be waiting for you.