Overlooks

 

Nestled at the crossroads of Kentucky, Tennessee, and Virginia, Cumberland Gap National Historical Park is a place where history and natural beauty converge. For centuries, this rugged mountain pass has been a gateway for pioneers, soldiers, and travelers seeking new frontiers. Today, visitors can experience the same breathtaking landscapes from four stunning overlooks, each offering unique vistas and a glimpse into the region’s past. Whether you’re looking for an easy drive-up viewpoint or a rewarding hike to panoramic mountain scenery, Cumberland Gap’s overlooks provide unforgettable experiences for every explorer.

 
View from the pinnacle overlook.
View from Pinnacle Overlook.

NPS Photo

Pinnacle Overlook

Location

  • Located at an elevation of approximately 2,440 feet.
  • Easily accessible via Pinnacle Road within Cumberland Gap National Historical Park.
  • Once you enter the park by the visitor center, take the first left. Follow the two-lane road four miles to the top of the mountain. At the top there is a short 150 yard walk to the overlook viewing platform.

Handicap Accessibility

  • Fully accessible with a paved path from the parking area to the overlook.

History: Then and Now

  • Then: Historically used as a strategic lookout during the Civil War. The overlook provided a vantage point for controlling passage through the gap.
  • Now: Today, it is the most visited overlook in the park, offering panoramic views of Kentucky, Tennessee, and Virginia. You'll see the historic Cumberland Gap, the town of Middlesboro nestled within the ancient Middlesboro Crater, and on a clear day you'll see the distant Great Smoky Mountains.

What You'll See

  • Stunning views of the Cumberland Gap, Powell Valley, Fern Lake, and the vast Appalachian landscape.
  • Best visited during sunrise or sunset for dramatic lighting over the mountains.

Seasonal Considerations

  • Spring & Summer: Lush greenery and clear skies make this an ideal time for visits.
  • Fall: The overlook offers a breathtaking view of the vibrant autumn foliage.
  • Winter: Road access to the overlook may be closed due to snow or icy conditions, so check park alerts before heading out.

 
Three markers in a triangle representing the different states.
Three markers at the overlook representing the three states.

NPS Photo

Tri-State Peak Overlook

Location

  • Located at the intersection of Kentucky, Tennessee, and Virginia.
  • Once you enter the park by the visitor center, take the first left. Follow the two-lane road for one mile, turn right onto HWY 988 then immediatly turn right into the Thomas Walker Parking Area. The trail starts at the head of the parking area on Object Lesson Rd Trail, connects to Wilderness Rd Trail and brings you into the Historic Cumberland Gap. Once in the gap, Tri-State Trail is on the right. Round trip this hike is 2.4 miles, from parking lot to the peak, and back.
  • Accessible via a moderate hike on the Tri-State Peak Trail.

Handicap Accessibility

  • Not fully accessible due to uneven trails, but the hike is moderate and well-maintained. The Object Lesson Road/ Wilderness Road Trail is gravel. The Tri-State Trail is a dirt path.

History: Then and Now

  • Then: The marker designates the settled line between North Carolina and Virgina in the 1780s survey. Later when Tennessee and Kentucky were created it became the Tri-State Peak, the exact location where Virgina, Tennessee and Kentucky meet.
  • Now: Visitors can stand in three states at once while enjoying sweeping views of the surrounding mountains.

What You'll See

  • A historical marker at the tri-state boundary.
  • Views of Middlesboro, Kentucky and the surrounding valleys.

Seasonal Considerations

  • Spring & Summer: A great time to visit, with comfortable temperatures and lush surroundings.
  • Fall: A must-see for leaf-peepers as the mountains transform into a canvas of red, orange, and gold.
  • Winter: Trails may be icy or muddy, so proper footwear is recommended. The hike can still be enjoyable, but caution is advised.

 
Overlook view from White Rocks
Overlook view from White Rocks.

NPS Photo

White Rocks Overlook

Location

  • Situated on the eastern edge of the Cumberland Gap in Virginia.
  • Travelling on Hwy 58, the exit for Civic Park Trailhead is located at mile marker 13.2, turn left onto Sand Cave Rd (State Road 724).
  • Accessible via a moderate-to-strenuous hike along the Ewing Trail or the White Rocks Trail.

Handicap Accessibility

  • Not wheelchair accessible due to rugged hiking trails.

History: Then and Now

  • Then: White Rocks served as a landmark for early pioneers and Native Americans traveling through the Gap. The bright limestone cliffs were visible from miles away.
  • Now: A popular destination for experienced hikers seeking breathtaking views of the Powell Valley and the surrounding mountain ridges. This also is a popular place for backcountry camping.

What You'll See

  • Expansive views of Virginia’s Powell Valley and beyond.
  • The striking white sandstone cliffs that give the overlook its name.

Seasonal Considerations

  • Spring & Summer: The trails are typically dry and filled with wildflowers and fungi, making for a pleasant hike.
  • Fall: Cooler temperatures and colorful foliage create a stunning backdrop.
  • Winter: Snow and ice can make the trails treacherous, and portions may be closed. Be sure to check trail conditions before heading out.

 
View from Powell Overlook.
View from Powell Overlook.

NPS Photo

Powell Valley Overlook

Location

  • Located along U.S. Route 58 in Virginia.
  • Once you enter the park, take the first left. Follow the two-lane road for four miles to the top of the mountain.

Handicap Accessibility

  • Not fully accessible as both trails to the overlook have multiple stairs to them, and a narrow path.

History: Then and Now

  • Then: Powell Valley was a crucial route for westward expansion, with settlers and traders passing through the area.
  • Now: The overlook provides one of the most iconic views of Powell Valley, frequently visited by photographers and sightseers.

What You'll See

  • A sweeping vista of Powell Valley, with rolling hills and farmland stretching toward the horizon.
  • Best visited in the fall when the valley is ablaze with autumn colors.

Seasonal Considerations

  • Spring & Summer: Clear days provide the best long-distance visibility.
  • Fall: A perfect spot for fall foliage photography.
  • Winter: Easily accessible year-round, but fog and snow may occasionally limit visibility.

Last updated: August 22, 2025

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Contact Info

Mailing Address:

91 Bartlett Park Rd.
Middlesboro, KY 40965

Phone:

606 248-2817

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