Cumberland Gap National Historical Park isn’t particularly well known. Wedged between Kentucky, Tennessee, and Virginia, the main entrance and visitor center is in Middlesboro, Kentucky. The visitor center is the best place to start, so you can buy tickets for the tours, get a map, and learn the history of the area. The 70 miles of hiking trails take you across all three states. The real star of Cumberland Gap is the cave system. The cave network is amazing. Some of it is open to tours, but much more of it is available to explore if you’re an experienced spelunker.

Some trails are easy, paved trails. Others are quite rustic and challenging. The staff at the visitor center will help you pick the right trail for you. The hiking trails are a lovely way to spend the day. Cumberland Gap is a great spot to stop on a road trip to get some fresh air and stretch your legs for a day or two.

The town of Middlesboro doesn’t have much to offer and you’ll need to drive into one of the neighboring areas if you’d like to buy booze, since Middlesboro is a dry town. It does offer all the (other) basics if you’re camping at the park. You’ll find that the park is more than enough to keep you occupied; you certainly won’t be bored.

Missing the road. . . #latergram #tunnel #blackandwhite #cumberlandgap

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If you’re a transit nerd like me, you’ll find the Cumberland Gap Tunnel interesting, too.

Cumberland Gap Caves

You can take a guided tour through Gap Cave. It takes about 2 hours and is not one of those caves with mini-trains to take loads of tourists through. If you’d like to fall to your death, there’s ample opportunity, so stick to the trail if you’d like to make it out. You’ll be in a small group or alone with a ranger and walking a mile to the cave and around 200 steps down. You’ll need closed toed shoes, like sneakers. You aren’t allowed to explore the cave on your own and will need to buy tickets.

I was in Cumberland Gap to visit a friend who was helping to map the trails and develop a guide to the Cumberland Gap cave system.


Hensley Settlement

Located on the top of Brush Mountain, the Hensley Settlement has been restored to show life in the early 1900s in this tiny, isolated village. It’s hard to imagine what life would be like living in a mountaintop settlement, but walking through makes the experience come to life. You’ll tour the blacksmith shop, springhouse, and schoolhouse on this tour that lasts about 4 hours. Tours go once a day, have limited seating, and can be booked up to a month in advance.

Tri-State Peak

You can catch a nice view of all three states from the Pinnacles. If you’d like to save yourself some effort, you can drive to the top, so long as you don’t mind a few hairpin curves. The road leaves from the visitor center and takes you from Kentucky to Virginia.

Wilderness Road Trail

The Wilderness Road Trail, also known as the Daniel Boone Trail, took pioneers across the Gap from Tennessee into Kentucky. It’s hard to imagine a time when this was truly wilderness, or Americans crossing anything on foot or by covered wagon. It’s not quite the Oregon Trail, but it’s a great hike and a fascinating history.

The Trails

The Cave

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