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.

the views made this completely worth it. trail is very very rocky and can be tricky footing when coming back down. there are several trails not marked on this map so be careful about where you turn. we took a wrong turn and added nearly 2 miles to our hike and made it much steeper. the sand cave was a lovely place to have lunch and cool off. the views from the white rocks summit made the extra elevation and distance nothing to complain about.

There's lots of shade and variations in flora as you progress through the trail. My favorite forested area is along the ridge near the side trail to Sand Cave because of the dense carpet of ferns covering the slopes. I had to put away the trekking poles and do a bit of a scramble to get up the final portion of the trail to the white rocks. It was certainly a well-earned view. As a hiker who is somewhere between the end of "beginner" and the beginning of "advanced", I'm grateful for my trekking poles. The descent would have been too hard on my joints without them. I chose to sacrifice a thicker, harder sole in my hiking boots in exchange for a lighter weight, and that decision led to bruised pads on my feet from this rock-strewn trail. A sturdier boot with ankle support would have saved me from some discomfort.

Very easy hike. Completed with my 5year old in tow. Well marked, maintained, and clean. Historical markers/info boards along the way. This would be a better hike for late fall to early winter when the foliage wasn’t blocking your views.

This trail is magical. I did it alone and didn’t pass one person. Of course the pinnacle is even busy on a Monday morning. Great workout too. Did it all in four hours with two stops at the overlooks. Didn’t see any wildlife

This trail is a more difficult hike compared to others in SWVA. The elevation increase isn't necessarily a steep incline, but it's over a long period of time. Returning back off of the mountain from white-rocks is an easy and quick descent. The trail itself and white rocks offers gorgeous views of the surrounding valleys and farm land. The sand cave is overwhelmingly large in person. It is a gorgeous site to see, and one that is truly unique and one of a kind. I strongly recommend it.

19 days ago

Amazing hike! Totally worth doing but is definitely a moderate trail. Took us about 4 hours to do Sand Caves and White Rocks. Dog friendly and absolutely gorgeous views. Sand Caves are absolutely spectacular.

Easy to follow trail with minimal incline. Great for dogs and is a nice leisurely hike for any part of the day.

Short trail with beautiful view of Middlesboro at the end. Pretty solid beginner hike, only took 1 hour and is great for dogs. Decent incline but manageable.

The first 3 miles is all up hill, gaining around 2,000 feet of elevation. Paths are well marked and the majority are very wide. When you get there the view from white rocks is well worth the up hill climb! And sand cave is awesome too! And of course the last 3 miles is all down hill. We started early on a “cool for July” morning and knocked out the 3.5 mile walk to white rocks in 2 hours and 5 minutes. Happy trails!

Well-kept trail, with plenty of easy-to-follow signs

Hiked it to Hensley Settlement first 3 miles are a strenuous climb but it’s all on a wide gravel access road. Visiting the settlement is worth it. Had the whole trail to ourselves on a Friday in July.

This was a very well marked trail with a steady incline for most of the first half. It took us 5 hours total to see both White Rocks overlook and the Sand Cave. Pretty strenuous overall but worth the trek!

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.

1 month ago

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.

1 month 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.

1 month 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
2 months 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.

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