Length/Type: Approximately 7.0 miles, loop trail; Difficulty: Strenuous (well-maintained trail throughout, but contains occasional rough footing and long, difficult climbs up and down Cumberland Mountain); Other Considerations: The park’s trails are well-signed and well-maintained. However, since this route makes use of multiple trails and contains several junctions that involve multiple intersecting trails and/or roadways, it is likely best to familiarize yourself with the park’s hiking map before you set out and have it with you during your trip.
Ask people who have visited Cumberland Gap National Historical Park what to see, and you’ll probably get told one thing: you need to hike to Sand Cave and White Rocks. These two destinations – a massive rockhouse and high, clifftop overlook, respectively – are definitely worth a look, and being able to hit both places in a single hike makes for an incredible trip…
…but the Sand Cave/White Rocks hike is overrated – so overrated, in fact, that we’ve intentionally chosen not to profile it so far on this site. Why the disdain? It’s simple: it’s nothing really about that hike itself but rather that the hike’s popularity acts to the detriment of equally impressive sites nearby. The same thing has happened at the famous (or infamous) Devil’s Bathtub in Scott County, Virginia. A smorgasbord of incredible hikes exist in the vicinity of the Bathtub, but they all sit empty while hordes of people crawl over each other to see the trail they heard about from their friends, many thinking it’s the only trail around.
The exact same phenomenon has happened in Cumberland Gap NHP. Visit the park on almost any warm weather weekend, and you’ll find a packed parking lot and slow-moving slug of people on the Ewing Trail, the main route leading to Sand Cave and White Rocks. Elsewhere on the park’s 85 miles of trails, though – yes, we said 85 miles! – you might not see another soul at all. That’s why we’ve decided to profile one of the hikes you’ve been missing, even if you think you’ve seen the best scenery in Cumberland Gap NHP. This one is a doozy (and you’ll need to be in good shape with some experience under your belt to tackle it), but it’s the perfect alternative to following the crowd.
This route is a good, old-fashioned loop hike: long enough to get you “out there,” tough enough to wear you out, and convenient enough to spit you back out at the car when you’re done. Beyond that, the scenery is excellent. You’ll be hiking along the base of Cumberland Mountain, straight up its south face, past a cave opening, and then along the ridgeline back through the famous Cumberland Gap itself. Be warned, though, that this isn’t just a walk in the park by any stretch. You need to be comfortable putting in some miles and hiking in steep and rugged terrain before you tackle this route. It probably shouldn’t be your first foray into the woods.
Begin the loop by parking at the Daniel Boone Parking Lot (see directions at the bottom of this post), the main trailhead used by hikers to access Cumberland Gap from the Virginia and Tennessee side of the park. If you’re there on a good-weather weekend during hiking season, expect to find the lot crowded with visitors wanting to hike the short distance to the Gap and the Kentucky state line. Don’t worry, though: you’re about to leave the crowds behind. Instead of heading left (west) from the parking lot, follow the Boone Trail to the east (right) from the trailhead. The Boone Trail doubles as a multiuse path, and it will likely be the easiest part of your hike, snaking on a wide treadway around the base of Cumberland Mountain. Use the easy hiking as a warmup, and you’ll reach the outskirts of the Wilderness Road Campground at 1.6 miles.
As the Boone Trail enters the vicinity of the campground, you will reach a paved road. While the trail crosses this roadway (turning into the Colson Trail), don’t follow it. Instead, turn left and begin to walk along the road itself. In about 0.2 miles, another road will branch off to the left. Turn left here to follow the road and immediately look for the Lewis Hollow Trail to cross the road near this junction (the Park Map can be a help here, since this junction is tricky). Turn left onto the Lewis Hollow Trail – the right fork leads into the campground – and begin to follow it up the mountain. You’ll pass the Lewis Hollow Connector Trail coming in from the right after 0.7 miles, but keep on the Lewis Hollow Trail proper, climbing up the mountain.
From its junction with the connector, the Lewis Hollow Trail gets down to business. There’s no sugarcoating it, either: this is a steep, long, hard slog straight up the face of Cumberland Mountain. The climb isn’t pointless, though, as you’ll pass the gated opening to Skylight Cave on the way up and witness the transition from drier, more open forests at the base of the mountain to a much more lush woods near the mountain’s summit. The beauty helps to take your mind off of the climb. After 0.8 miles of grunting up the mountain, you’ll reach the top of the ridge and the aptly-named Ridge Trail 3.3 miles from the original trailhead.
The Ridge Trail serves as the main backcountry artery through Cumberland Gap NHP. From its junction with Lewis Hollow, the Ridge Trail runs east several miles to the Hensley Settlement (another must-see destination in the park) and then a few more miles to its end near White Rocks. Our route for this hike will instead turn left, following the Ridge Trail to the west and back towards Cumberland Gap itself. Note that the Sugar Run Trail also comes up and joins the Ridge Trail from the Kentucky side of the mountain near where the Lewis Hollow Trail ends. Ignore this route and follow the Ridge Trail to remain on this hike.
It’s 1.7 miles along the Ridge Trail to the next leg of this hike, and this stretch is one of the most beautiful and enjoyable parts of the loop. The Ridge Trail isn’t sidewalk flat, but it’s a nice reprieve from the climb up Lewis Hollow. And since you’re on the ridge, you’ll be treated to some scenery. A few limited views through the trees can be had from rock outcrops just off the trail, and winter months will bring almost steady views off to the south. If you’re craving a sweeping, panoramic vista, though, just wait: you’ll enter the park’s Pinnacle Overlook at 5.0 miles from the start of the hike. This isn’t a wilderness vista – there’s a nearby parking lot, and the overlook itself has interpretive signs and a railing – but that scarcely matters thanks to the view. On a clear day, the Great Smokies loom in the haze on the horizon. The Powell River Valley spreads out below you, with the town of Cumberland Gap, Tennessee some 1,000 or so vertical feet straight down.
Enjoy the view and the Pinnacle’s numerous historical markers, and then continue following the trail downhill (the route bears left and down when walking back from the overlook) for 0.8 miles to a pull-out on Pinnacle Road. The Harlan Road Trail crosses the road here, and you’ll want to follow it to the left, downhill and out the back of the pullout, around 0.3 miles to the famed Cumberland Gap. You’ll cross the road again on the way down. Once you’re in the Gap, you’ll reach a junction with the Wilderness Road Trail. Turn left here to cross through the Gap, head back into Virginia, and reach your car at the original trailhead in 0.9 more miles. Stay straight past the spur trails on this section, although you may want to check out the signed sidetrip to gated Gap Cave on the way.
Where can you start with nature notes for this hike? Cumberland Gap NHP literally has it all, and this route samples a bit of everything. You’ll travel through karst (limestone) terrain during much of the route, passing by two cave entrances and witnessing a bit of their unique ecology. On your climb up the mountain, you’ll witness an ecological transition of forest types as you leave the drier valley floor for more moist hillsides above. Wildlife abounds across much of this entire route.
Arguably the biggest natural feature on this hike, though, is Cumberland Gap itself. The Gap may not seem like much while you’re hiking through it, but there’s no denying how important this single geographic feature is to Virginia, Kentucky, and Tennessee. Heck, the history of North America itself hinges in many ways on this one gap in the ridgeline. Prior to human habitation, this gap was likely a natural passageway for ancient Appalachian “megafauna”: things like mammoths, musk ox, and (later on) buffalo and elk. Native Americans also used the gap in a similar manner as a relatively easy route through the otherwise impenetrable ridge of Cumberland Mountain.
European settlers came along in the 1700s, namely Daniel Boone and his traveling party, and opened up a route to the western frontier using the Gap. Thousands of people passed through here in ensuing years, hoping to find prosperity in what seemed to them to be a new world. The Gap was used as a strategic location during the Civil War just under a century later, and a highway (US-25E) even passed through the Gap in the 1900s. After the highway was rerouted through Cumberland Gap Tunnel in 1996, the route through the Gap became a true trail once again.
There’s literally so much history, ecology, and geology packed into this one spot that we couldn’t even begin to do it justice here. Do yourself a favor and visit the Cumberland Gap NHP Visitor Center on the opposite side of the mountain after your hike. You’ll be glad you did.
Directions: From the junction of US Highway 25E and US Highway 58 just north of Harrogate, Tennessee, take US-58 east a short distance to the signed exit for Cumberland Gap and the Daniel Boone Parking Area. The large parking area and trailhead are on the right shortly after exiting the highway.