Looking for a great trail in Cumberland Gap National Historic Park, Virginia? AllTrails has 16 great hiking trails, trail running trails, dogs leash trails and more, with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers, and nature lovers like you. Ready for some activity? There are 9 moderate trails in Cumberland Gap National Historic Park ranging from 1.2 to 18.6 miles and from 1,269 to 3,461 feet above sea level. Start checking them out and you'll be out on the trail in no time!



dogs on leash



nature trips

trail running


wild flowers

kid friendly

Mountain Gateway At Cumberland Gap, the first great gateway to the west, follow the buffalo, the Native American, the longhunter, the pioneer... all traveled this route through the mountains into the wilderness of Kentucky. Modern day explorers and travelers stand in awe at this great gateway and the many miles of trails and scenic features found in the park.

We really enjoyed this trail! The elevation gain was challenging enough without being difficult, but I would say you either need to be in shape or work in time for plenty of breaks. You cross a creek several times. A little less than a mile from the Pinnacle is an unnamed lookout that was gorgeous and not crowded like the Pinnacle. The trail is not marked but super easy to follow. We had our hiking poles and found them to be very useful. We ended up with a little over 9 miles (including walking around the Pinnacle) and just over 4.5 hours.

A nice short hike, about 1.5 hours total. There was not a great view from the top, just a lookout over Middlesboro, KY. There were nice monuments and informational signs along the way. The town of Cumberland Gap where the trail begins is really quaint as well.

I did this hike from Thomas Walker parking lot. Follow The Thomas Walker trail about 50 yards to Wilderness Road Trail to the gap then up to Tri-peak. If you go past the pavilion, you can hike to an old civil war fort. I hiked Object Lesson back to parking lot. The recording for this trail actually follows Object Lesson.

10 days ago

Great trail to build endurance. The ascend is a bit strenuous is you aren’t an active hiker, however the views are definitely worth it. The trail was decently trafficked, especially with horseback riding groups, but the trail is plenty wide enough to provide space for passing. The sand cave is magnificent and wasn’t as crowded as we had initially thought. The short hike over to the white rocks is absolutely worth it. It’s a quick, but vigorous trek to the top overlook. But the 360 view is amazing! Be sure to bring plenty of water and something to snack on! This took us about 4 hours, taking our time and enjoying the scenery.

Excellent hike, took us roughly 6 hours to hike 9.8 miles. We went the long way going in and took the shortcut on the way back. I think “moderate” is not the correct classification due to the 4 mile uphill climb all the way to the stunning, jaw dropping Sand Cave (2,595’ elevation gain). As another reviewer stated, photos don’t do it justice... This is a must do for your bucket list! The views from White Rock overlook are incredible, the sheer drop offs will make yours knees wobble too... I would highly recommend this hike, take plenty of liquids and snacks/lunch... As a side note, there was a rattlesnake on the trail, keep your eyes open and don’t step on one...

Vigorous hike but definitely worth the climb!!! The sand cave is incredible and White Rock Overlook was absolutely beautiful!

Great trail to bring dogs! The trail was wide and although inclined in some areas, was very easy to navigate. Highly recommend!

The sand cave was something out of a dream, no pictures will do it justice. The trek up was pretty intense but it was worth it.

Great hiking trail, as I read from other post more of a moderate trail due too the incline. Dogs and kiddos approve. Disappointed at the top, really no view.

20 days ago

Trail was very clearly marked and shady! The hike is straight up hill the entire way to tri-state marker but so fun once you get to the top and get to stand in three states! Super easy hike back down since all down hill!

Nice and fairly easy hike. well maintained.

Moderate, steady incline. Was able to keep a consistent pace and the trail was wide enough the two of us walked next to each other and had light conversation without getting winded. The caves are SO AWESOME. Took our boots off and played in the sand for a bit, stopped for lunch and to cool off by the water droppings. The views are great too, but we did the cave first which was the highlight of the hike. We saw a deer, lots of toads and lizards, a couple of snakes and some wildflowers as well as berries. Great day out in nature. Only passed one other family while we were there.

on Gibson Gap Trail

over grown
1 month ago

The trail started out good. We knew the trail was going to be a hard one, but was told it would be marked. We hiked 1.2 without any trouble. When we got to a road left was a private road , right took you back down. Called ranger station and they said bare to right . We went right, left, up , and down, but we could not find a trace of the trail. Did not feel safe going any futher. We did let ranger station know so they would not send anyone else up there.

I highly recommend this trail because it's relatively easy, well kept and the views are absolutely beautiful.

The cave is amazing!

The moderate rating is appropriate for this trail. The views were worth the climb. The Sand Cave felt amazing on my feet

The trail is very well maintained with plenty of markers. I would not categorize this hike as easy though. More moderate. It is steep on the way up and an ankle breaker on the way down but the payoff is worth it!

loved the area ,beautiful trail and overlook is amazing .

loved this area very beautiful trail and once to the top ,the overlook is amazing .it is uphill pretty much all the way to the overlook but worth it ..

love it. great challenging hike. backpacking overnight and staying at the tent sites up there was good. did hike twice. sand cave is huge and stunning. water was flowing in spring so able to filter water

I love this place. Many things to see.

over grown
2 months ago

Southeastern Kentucky Hikers event. We had nine hikers. The trail was very green, and full of nature. The highlight of the trail is Skylight Cave. We had absolutely no issues (no snakes, no falls, and I personally didn't have any ticks.) The trail was over grown in areas and it was impossible to avoid contact with weeds, etc. Difficulty: I rate it as moderate. There wasn't anything that the average hiker could not do, but it does have a lot of elevation and it is long. Make sure you bring enough water! Parking: We parked in a parking lot and hiked the 0.8 mile Colson Trail to get to Gibson Gap Trail. There was plenty of parking in that parking lot. Will I hike it again: YES. Overall it was a great trail, but I will hike this trail during the colder months to maximize the view from the ridge line. And also to minimize contact with ticks and weeds.

2 months ago

So freakin pretty! I went on a Friday and didn't see another soul the entire time. The cave was amazing. Never before had I seen anything like it. Saw multiple frogs on the trail but no other animals.

This place is so beautiful. The hike with 3 kids was interesting but when we got there it was so worth it

Very scenic hike, the cave is absolutely stunning. Bring plenty of water!

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