Cumberland Gap Hike: White Rocks, Sand Cave and Hensley Settlement

By Jeremy Patton

White Rocks, Sand Cave and Hensley Settlement are located in Cumberland Gap National Historical Park. The park resides in three states: Kentucky, Tennessee and Virginia.

Jeremy Atop White Rocks Overlook 10/23/16

Jeremy Patton atop White Rocks Overlook 10/23/16

This article will summarize a long hike that I took with some friends on 10/23/16. I will write detailed articles about the trails and landmarks later.

In mid October, Russell Kersey invited me on a 10-mile hike from Civic Park to White Rocks and Sand Cave. We had never met in person, but Russell seemed like an experienced hiker who could keep up with me, so I agreed.

Several days later, he proposed an amended route that included the Hensley Settlement, increasing the distance to about 12 miles. I accepted reluctantly because I was not in proper shape for a long trek so early in the season.

I was the first to arrive at our meeting place at Cumberland Gap Visitor Center in Middlesboro. As I waited in the morning mist, a family of deer emerged from the woods and paraded in front of my car — a good omen.

Russell and his friend Steve Madden soon arrived. We drove through the Cumberland Gap Tunnel then parked at two locations in Virginia so that we could shuttle from one trailhead to the other.

We turned off US-58 and headed toward Civic Park, which is located near the eastern-most edge of Cumberland Gap National Historical Park. A panorama of the soaring White Rocks soon came into view. Steve yelled for the car to halt then jumped out into the middle of the road to snap some photos. I joined him.


From Civic Park, we set off climbing the mountain via Ewing Trail.

I soon asked “how many miles for this hike?”

“12 or 13,” Russell responded.

Steve, a 59-year-old distance hiking enthusiast, looked back at me and snickered. That was when I knew that I was in for a long day.

The nearly 3-mile trail to the ridge was difficult, but well-maintained with forgiving switchbacks. The scenery was beautiful, but nothing spectacular aside from a few partial overlooks of the Virginia valley.

A partial overlook on Ewing Trail 10/23/16

Ewing Trail 10/23/16

Atop the ridge, we located the side trail for White Rocks Overlook. A sign indicated 0.8 miles to the top. It felt every bit of that distance due to its steep grade, but I believed it to be shorter. Throughout the trip, the mileage estimates on the trail signs contradicted each other. Any estimates that I offer here are uncertain.

White Rocks Overlook Trail led to a few natural overlooks. The views were fantastic, but I concurred with Steve that I would have rather looked upon wilderness than farmhouses. With that said, the climb was worth it and I intend to journey there again.

Russell led us further along the cliff-line. We went off-trail and climbed up some boulders to a higher, hidden perch. There we found additional overlooks that were more spacious and less visited. We enjoyed the spot alone.

Russell Kersey atop White Rocks Overlook 10/23/16

Russell Kersey atop White Rocks Overlook 10/23/16

White Rocks

White Rocks

To our right rose a forested peak that Russell identified as the highest in the park. He had read that a path led to the summit where a plaque marked the elevation at over 3500 feet. We did not find the path, but intend to search for it on a future visit.


We made our way back down then continued west on Ridge Trail. We soon saw a sign that confirmed our upcoming objectives: Sand Cave and Hensley Settlement. It listed Hensley Settlement at 4.5 miles. We proceeded for at least half a mile, then saw another sign. It said “Hensley Settlement 4.5 Miles.” Either it was Groundhog Day or someone did not know how to measure distance.

After about a mile, we reached the trail for Sand Cave, a short, but hilly stroll labeled on one of my maps at 0.2 miles. Sand was deposited within the massive rock shelter in such high volume that it felt like walking on the beach. It was unlike any rock shelter that I had ever seen. A waterfall resided near its gaping entrance, but was a mere trickle due to an ongoing drought. I look forward to returning during wet weather.

Sand Cave 10/23/16

Sand Cave 10/23/16

We back-tracked to Ridge Trail then marched toward Hensley Settlement. My friends led a pace that made me feel like I was at the races. I was in better shape than I expected, so the mileage did not bother me. It was the grinding speed.


We zoomed by numerous rock formations and partial overlooks that I wanted to examine, but each time I stopped to investigate them or take a photo, I found myself further behind. The lagging probably made me appear to be a less than competent hiker.

Why do I hike so slow? I probably developed the habit because I often explore solo and off-trail in the most remote areas that I can find. Slower hiking reduces the risk of injury and increases awareness of your surroundings. Twisting an ankle or getting caught off guard by an angry mama bear is bad, but more dangerous when alone.

The trek prompted me to analyze why I hike. For me, quality is more important than quantity. I like to explore areas thoroughly, often returning to them again and again. I need time to piddle around, to relax — to think.

I do see the value of high mileage hikes, however; my first visit to White Rocks, Sand Cave and Hensley Settlement was a primer that armed me with useful information for planning future objectives.

We finally arrived at Hensley Settlement, established in 1904 and occupied until 1951. Restored log cabins, a one-room schoolhouse and a blacksmith shop resided there. We were interested in viewing the local cemetery, but had trouble locating it.

A cabin at the Hensley Settlement on 10/23/16

A cabin at the Hensley Settlement on 10/23/16

We had the grounds to ourselves. Steve spoke at length on how it reminded him of Cades Cove in the Great Smoky Mountains, but better because it was less crowded.

Russell Kersey and Steve Madden at Hensley Settlement

Russell Kersey and Steve Madden at Hensley Settlement

Although I prefer spending time in wild and relatively untouched places, the rustic cabins, rolling hills and vivid fall colors were inspiring. I immediately understood the allure of the lonely settlement atop Brush Mountain. The lack of people made it even more appealing.


After rest and a snack, we retraced our steps east then started down Chadwell Gap. It was the antithesis of Ewing Trail: scenic, steep and dangerous. Russell fell several times, sliding on loose dirt and acorns; I had a couple of close calls.

Chadwell Gap

Chadwell Gap

The fast pace bothered me here the most. It beat up my legs, jarring by hips and knees. But back at Hensley Settlement, I had expressed my desire to get down the mountain before dark, so I had no room to complain about the urgency.

Russell and Steve waiting for me to catch up

Russell and Steve waiting for me to catch up

We finally arrived at Chadwell Gap Parking Lot at twilight, on wobbly legs. Russell and Steve made several jokes at my expense, along the lines of “yeah, Jeremy will never hike with us again.”

Yes, I will. Time has a way of making you forget the aches and soreness of a long hike. Comradery and memories make it all worthwhile.

What was the total distance for the day? Steve said about 14.5 miles; Russell estimated 16. I will go with 15 miles. Regardless, this was a strenuous trek for advanced hikers.

Added 10/31/16