With miles of trails ranging from short scenic walks to challenging backcountry routes, the park offers opportunities to explore sweeping views, quiet woodlands, and landscapes rich with history. Whether planning a quick outing or a full day on the trail, there are routes suited to many skill levels.
Photo by Olivia Paul Handicapped Accessible TrailsSeveral trails are designed to be accessible so that more visitors can experience the park's landscapes. These routes offer smoother surfaces, gentler grades, and features that make them easier to navigate with wheelchairs, mobility aids, or strollers.
Hiking Trails
NPS Photo/ Olivia Paul 
NPS Photo/ Chandler Shepherd 
NPS Photo 
NPS Photo/ Olivia Paul Trails Enjoy this short walk in the fresh mountain air out to our most visited overlook in the park. From the Pinnacle on a clear day, you will see three states and 100 miles into the distance. This can also be a starting point for longer hikes either out and back or shuttled with a friend and two vehicles.
Duration: 5 minutes Miles: 600 ft one way Trail Difficulty: Easy Location: Pinnacle Overlook Parking Area This historic hike follows the old gravel roadbed of Object Lesson Road. With a slight incline the whole way to the Cumberland Gap, you will enjoy an easy stroll back to the parking area on your way back. This hike can easily be extended to include other trails.
Duration: 20 minutes one way Miles: 0.4 miles one way Trail Difficulty: Easy Location: Thomas Walker Parking Area The medium intensity elevation ups and downs of Fitness Trail are perfect for getting your heart rate up and some fresh air without the time commitment of a long hike. This trailhead also conveniently creates a loop right back to the Visitor Center parking area and has many daily visitors.
Duration: 45 minutes total Miles: 1.8 miles loop Trail Difficulty: Easy to moderate Location: Visitor Center. This trail stays closely parallel to Pinnacle Road. This out and back hike is great if you are wanting to experience a nice straight hike that isn’t too far from a roadway. This hike can also be extended onto other connecting trails for a longer hiking experience.
Duration: 30 minutes one way Miles: 1.1 miles, one way Trail Difficulty: Easy to moderate Location: Visitor Center Parking Area or Thomas Walker Parking Area If you enjoy history, there is not better hike than Wilderness Road. This hike takes you past many historic areas, including straight through the historic Cumberland Gap Pass. You can easily extend or shorten this hike to hit the highlights you are looking for or avoid strenuous areas.
Duration: 1.5 hours one way Miles: 2.4 miles one way Trail Difficulty: Easy to moderate, some strenuous areas Location: Thomas Walker Parking Area or Daniel Boone Parking Area This elevation grabbing hike is one of the most popular in the park. The destination is the top of Tri-State Peak where you can stand in TN, KY, and VA all at once with an overlooking view of the town of Middlesboro, KY.
Let it be known that you must hike at least one half mile of other trials before you ever access Tri-State Peak Trail. Making this hike a minimum of 1.2 miles one way to reach Tri-State Peak. Duration: 30 mins one way on Tri-State Peak Trail only Miles: 0.6 mi one way on Tri-State Peak Trail only Trail Difficulty: Moderate Location: Branched off from Wilderness Road Trail This trail is a nice place to see wildflowers and some wildlife that enjoys a wetter ecosystem. There are a few wetland bridges that assist you in your fairly straight stroll between Daniel Boone Parking Area and a parking lot near Wilderness Road Campground.
Duration: 40 minutes one way, hiking Miles: 1.6 mi. Trail Difficulty: Easy to Mildly Moderate Location: Daniel Boone Parking Area and parking lot near Wilderness Road Campground This challenging, low traffic, out and back hike can easily be turned into a shuttled hike of varying distances with a friend and two vehicles or part of a longer loop using connecting trials.
Duration: 2 hours one way Miles: 2.3 miles one way Trail Difficulty: Moderate to strenuous Location: Fort McCook Parking Area, Highway 988, Dark Ridge Overlook, or Via the Sugar Run Trail from Sugar Run parking Area. This difficult trail connects Fort McCook and Pinnacle Overlook and is a low traffic hike that somewhat parallels Pinnacle Road. This hike can be extended onto to several other trails or a hike that can be a shuttled trip with a friend and two vehicles.
Duration: 35 minutes one way Miles: 0.8 miles one way Trail Difficulty: Moderate to Strenuous Location: Fort McCook Parking Area or Pinnacle Overlook Parking Area Ridge trail is sometimes section hiked but is most often used as a backcountry camping trail. This rugged trail has many iconic sites along the way but is difficult with over 11,000 feet of elevation change between Pinnacle Overlook and Civic Park. To camp on Ridge Trail, you do need a permit and reservation. Please call the Visitor Center for more information.
Duration: 1-3 days typically Miles: 19-21 miles from Pinnacle to White Rocks Trail Difficulty: Moderate to Strenuous Location: Pinnacle Overlook Parking Area is the most direct access to Ridge Trail. It can be accessed by several other trails throughout the park as well. This steep trail is a popular hike for those who enjoy solitude, running water, ferns and spring flowers. This trail can be tied into several other trails or made into a large loop as well.
Duration: 2.5 hours one way Miles: 2.5 miles one way Trail Difficulty: Starts easy and quickly turns strenuous Location: Sugar Run Picnic Area This hike is mostly used by people who want to see Skylight Cave. While this small cave is closed from September to May, it can be viewed from the trail year around. This hike is pretty well straight up and sparsely used once you pass Skylight Cave. It can be a potential shuttle hike with two cars and a friend when used in combination with connecting trails.
Duration: 1 hour one way Miles: 1.7 miles one way Trail Difficulty: Strenuous Location: Wilderness Road Campground or 0-4 Picnic Shelter This elevation grabbing trail is popular for people who want to work hard for some National Park gems. You can expect lots of switchbacks, wet trails in rain season, and slippery conditions. This trail is stunning view after stunning view until you reach Ridge Trail where both White Rocks and Sand Cave are close by. To camp on Ridge Trail, you do need a permit and reservation. Please call the Visitor Center for more information.
Duration: 2 hours one way Miles: 2.5 miles one way Trail Difficulty: Strenuous Location: Civic Park This steep hike is the shortest access point to Hensley Settlement via Ridge Trail. Expect elevation gain, solitude, some rocky terrain and beautiful views. To camp on Ridge Trail, you do need a permit and reservation. Please call the Visitor Center for more information.
Duration: 2.5 hours one way Miles: 2.8 miles one way to the Ewing Trail intersection Trail Difficulty: Strenuous Location: Chadwell Gap Parking Area This long uphill trail is for people who enjoy longer hikes right off the campground or backpackers accessing Ridge Trail. You will find wildflowers in the spring and creek crossing along the way. To camp on Ridge Trail, you do need a permit and reservation. Please call the Visitor Center for more information.
Duration: 4 hours one way Miles: 4.3 miles one way Trail Difficulty: From easy to Strenuous Location: Wilderness Road Campground 
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Last updated: March 11, 2026