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Dr. Thomas Walker of Albemarle County, Virginia is credited with discovering the pass in 1750 while searching for settlement sites beyond the mountains.
In 1775, Daniel Boone, along with thirty other men, were hired to blaze a trail, later known as the Wilderness Road, from Martin's Station (Rose Hill, Virginia) through Cumberland Gap. It would become the main artery for pioneer migration into the trans-Appalachian wilderness for the next 50 years.
Cumberland Gap National Historic Park
Known as the first great gateway to the west, Cumberland Gap is a prominent V-shaped indentation in the Cumberland Mountains that was used by wildlife, Native Indians and pioneers wishing to pass through the mountains. The Gap is situated on the Kentucky-Virginia boundary approximately one-quarter mile north of the point where Kentucky, Virginia, and Tennessee meet.
In 1940 Cumberland Gap was designated as a National Historical Park, making it the largest unit of its kind at that time (Chaco Culture is now the largest National Historical Park).
Today the park stretches for 26 miles along Cumberland Mountain. It occupies roughly 24,000 acres along the Kentucky, Virginia, and Tennessee border, and contains roughly 85 miles of hiking trails. There are numerous scenic and historic features within the park. Ranger led programs are also offered throughout the year including tours of Gap Cave and the historic Hensley Settlement.
From the Visitor Center, park visitors have the opportunity to drive a winding four-mile-long road up the mountain to the Pinnacle Overlook (elevation 2,440 feet) which offers spectacular views of the three surrounding states.
For most of the 20th century, U.S. Highway 25E cut a path across the Gap. However, after the completion of the Cumberland Gap Tunnel in 1996, the road was rerouted under the park. The Park Service is in the process of restoring the original appearance of the Wilderness Road as it crosses the Cumberland Gap. The replanting of thousands of seedlings from original forest stocks in the area is intended, over a period of decades, to recreate a forest that will allow visitors to view the crossing of the Gap as travelers would have experienced it the late 18th century. This section of the Wilderness Road is now a hiking trail.
The park offers a variety of outdoor activities such as hiking, backpacking, camping, wildlife viewing, as well as many opportunities to experience history first hand, including pioneer settlements and Civil War artifacts.
The lush vegetation of Cumberland Gap supports diverse animal life including: white-tailed deer, black bears, bobcats, gray fox, rabbits, raccoons, opossum, gray squirrels, hawks, vultures and wild turkey. The autumn hawk migration is usually spectacular and can be observed from numerous vantage points along the Ridge Trail as well as from the Pinnacle overlook.
Hiking in Cumberland Gap
Roughly 85 miles of hiking trails meander through eastern deciduous forest of Cumberland Gap. Distances range from a 1/4-mile loop trail to the 21-mile-long Ridge Trail. Some of the most popular destinations in the park include the Hensley Settlement, White Rocks, Sand Cave and Tri-State Peak.
Towering 3,500 feet above the valley floor, White Rocks is a massive limestone outcropping that offers breathtaking views into Virginia. The shortest hike to White Rocks is from Civic Park on the far eastern end of the park on the Virginia side.
Sand Cave is a 75-foot high sandstone overhang that is decorated by at least seven different colors of sand. In rainy seasons, a small waterfall cascades over the edge.
Another popular destination is Tri-State Peak which leads to the point where Tennessee, Kentucky, and Virginia meet.
Cutting across the length of the park is the Ridge Trail. This is a moderate trail with many ups and downs that runs along the Virginia/Kentucky border. The trail connects to all the major park trails, to four primitive backcountry campgrounds, and provides access to the Hensley Settlement, Skylight Cave, Sand Cave, and White Rocks.
The table below shows the 11 trailheads offering access to trails in the park, and the mileage to the various destinations within the park.
Please note that the former Chadwell Gap Trailhead off of Rt. 688 near Caylor, VA has been closed as a result of the trailhead being located on private land.
to Sugar Run 1.7
to Lewis Hollow Trail 1.7
to Gibson Gap Trail 5.1
to Indian Rock 10.5
to Hensley via Indian Rock 11.0
to Hensley via Ridge Trail 11.7
to Chadwell Gap 12.4
to Martin's Fork Cabin 12.6
to Chadwell Gap Trail 12.8
to Ewing Trail 15.6
to Sand Cave Trail 15.8
to White Rocks Campground Trail 16.5
to White Rocks 16.6
to Civic Park 19.0
to Ridge Trail 3.8
to Sand Cave Trail 4.0
to White Rocks Campground Trail 3.0
to White Rocks 3.2
to Martin's Fork 7.2
to Hensley Settlement 8.0
to Hensley Settlement 4.6
Wilderness Road Campground:
to Gibson Gap Trail 4.8
to Honey Tree Spur 1.1
to Green Leaf Nature Trail 0.1
Wilderness Road/Mischa Mokwa:
to Ewing Trail 21.0
Wilderness Road Picnic Area:
to Skylight Cave 0.6
to Ridge Trail 1.1
to Pinnacle 2.8
Highway 988 via Sugar Run:
to Ridge Trail 2.2
to Pinnacle 3.9
to Fitness Trail 2.0
to Bike Trail 1.0
Iron Furnace/Wilderness Road:
to Wilderness Road 0.3
to Saddle of the Gap 0.6
to Tri-State Peak 1.2
Thomas Walker Parking Lot/ Wilderness Road Trailhead:
to Saddle of the Gap 1.1
Thomas Walker Parking Lot/Object Lesson Road Trailhead:
to Wilderness Road 0.4
to Saddle of the Gap 0.6
to Tri-State Peak 1.2
Cumberland Gap Trail Map (10.1 mb PDF File)