When Daniel Boone passed through the gap in the Cumberland Mountains, I wonder if he took a moment to appreciate the stunning view from a particular rocky outcropping? Today, it’s much easier for visitors to find that outcropping and appreciate the view. A long drive on the winding Skyland Road and a short walk on a paved trail leads to the Pinnacle Overlook – and a stunning view of three states.
I visited Cumberland Gap National Historical Park for the first time in 2012. I was on a road trip adventure with the grandmother to Oneida and Jellico to trace our family’s genealogy. The grandmother was accustomed to making many stops when road tripping with me, so it was no problem when I drove the road to the top of the mountain to find the Pinnacle Overlook.
I’ve returned to the national historical park a few times since, but I still have much to explore. The Pinnacle Overlook remains the single activity I’ve done the most in the park. Here is everything you need to know to find and enjoy that stunning view – along with a few other tips to make the most of your trip.
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Cumberland Gap National Historical Park
Native Americans had been passing through the V-shaped cut in the Cumberland Mountain range for centuries. But when Dr. Thomas Walker discovered the pass in 1750, it opened the area to frontier settlers eager to cross beyond the Appalachian Mountains.
In 1775, Daniel Boone was hired to blaze a trail from nearby Martin’s Station – you can find a replica of the frontier fort at Wilderness Road State Park – through Cumberland Gap into the Kentucky Territory.
When Cumberland Gap National Historical Park was founded in 1940, it was the largest national historical park in the country. Although it’s no longer the largest, the park still covers a whopping 24,000 acres across the mountain range. The park features 85 miles of hiking trails, Gap Cave and Skylight Cave, and the Hensley Settlement.
91 Bartlett Park Road, Middlesboro, KY | 606-248-2817 | www.nps.gov/cuga
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Skyland Road
The Cumberland Gap National Historical Park Visitor Center is located in Middlesboro, Kentucky – just on the other side of the tunnel from Cumberland Gap, Tennessee. With a small museum to explore the area’s history and an information desk, the visitor center is a great place to begin an adventure to the Pinnacle Overlook.
Skyland Road – on most road maps, it is labeled Pinnacle View Road – is a 3.7-mile two-lane road connecting the visitor center with the parking lot at the Pinnacle Overlook. The Wilderness Road Trail Parking Lot is located on this road at the mountain base before the adventure to the top begins.
Skyland Road includes several switchbacks – or hairpin curves – between the mountain’s base and the Pinnacle Overlook parking lot. Visitors can take their time on the out-and-back road without feeling any pressure from pesky locals to hug the curves like a stock car racer. At a good pace of about 10 mph, it only takes twenty minutes to reach the top of the mountain.
The journey up was fun but coming back down was a little different. I shifted my Ford Explorer into the lowest gear possible, but I still had to ride the brakes descending from the parking lot. I pulled over at the visitor center to give the brakes a chance to cool down.
Pinnacle Overlook
The parking lot at Pinnacle Overlook was a bit deceptive. Surrounded by trees and thick vegetation, I would have had no idea the scenic overlook was just a few minutes away. The trailhead is almost hidden at the parking lot’s edge, unmarked, near the handicap parking spaces.
The hike from the parking lot to the scenic overlook is only a quarter of a mile along a paved path. About halfway there, I found a thick white line painted across the black asphalt. Standing on either side of the line, I was simultaneously standing in Virginia and Kentucky. Finally, after years of practice, I was in two places at once.
The first time I visited the Pinnacle Overlook, the view literally took my breath away. Leaving the canopy of leaves behind, I stepped out into the open on a stone floor and walked to the edge of the overlook at a waist-high wall. I scanned the 180-degree panorama view when I caught something in the corner of my eye – far below, a turkey vulture soared through the air. Far below, I thought to myself with a little laugh. It was like I was walking on the clouds.
The Pinnacle Overlook offered a stunning view of three states: Kentucky to the right, Tennessee straight ahead, and Virginia to the left. In the distance, I could see the sprawling mountain town of Middlesboro. And far below – in what was a rare opportunity to stand almost directly above a town – was Cumberland Gap. I had lunch down there later at the Gap Creek Coffee House.
I have been to the Pinnacle Overlook at Cumberland Gap National Historical Park three times now – and each time, the view is spectacular. At 2,440’, the overlook doesn’t set any records. But with a view like that, who cares about records?
Cumberland Gap Tunnel
The Pinnacle Overlook offers a really great view of the gap in the Cumberland Mountains. When U.S. Highway 25E was built through the gap, the contractors blasted a path in the mountains. But when the Cumberland Gap Tunnel was completed in 1996, engineers for the National Park Service restored the gap to its original layout.
Today, the Wilderness Road Trail retraces the route blazed by Daniel Boone through the Cumberland Gap. The 2.5-mile trail connects parking lots on the Kentucky and Virginia sides of the park. The hike includes a 240’ total ascent and takes about an hour to hike between the parking lots.
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Pinnacle Overlook Trail
If you’re up for a more adventurous journey to the scenic overlook, you might be interested in the Pinnacle Overlook Trail. The 7.8-mile out-and-back trail begins at the Sugar Run Picnic Area along Pinnacle Road and includes a hike on the Sugar Run and Ridge Trails.
The hike begins with a 2.1-mile hike on the Sugar Run Trail that includes the majority of 1,804’ total ascent. The trail intersects the Ridge Trail that runs the Cumberland Mountain range through the national historical site. At the intersection with the Ridge Trail, is it just another 1.5 miles to the Pinnacle Overlook.
Where to Stay
I absolutely believe the Pinnacle Overlook is worth an overnight trip just to see. However, lodging options are few surrounding Cumberland Gap National Historical Park – and I’ve chosen poorly in the past. Here are four places I recommend for spending the night.
The Wilderness Road Campground is a great place to spend the night camping inside the national historical park. Located off U.S. Highway 58 in Virginia, the campground is about a twenty-minute drive from the visitor center and a forty-minute drive from the overlook parking lot. With 160 campsites – 41 of which include electrical hookups – it would be a great place to stay.
The Olde Mill Inn Bed & Breakfast doesn’t look like much on the outside, but inside it’s a comfortable place to spend a night or two. The B&B is located inside a two-story clapboard house attached to an old log cabin – and the bedrooms are spread throughout both. Cumberland Gap’s location makes it convenient to the overlook – in fact, you can look up from the parking area to see it!
In Middlesboro, my top recommendation for a place to stay is the Holiday Inn Express. Rooms include one or two beds, or you can get the King Suite with a king bed and sleeper sofa for traveling families.
The Sleep Inn is a more expensive option that includes similar rooms – options for one or two beds or a King Suite with sleeper sofa.
