Ridge Trail: Pinnacle Overlook to Lewis Hollow Trail

By Jeremy Patton

Ridge Trail is located in Cumberland Gap National Historical Park in Bell County, Kentucky and Lee County, Virginia.

Ridge Trail Overlook #1 on 10/16/16

Ridge Trail Overlook #1 on 10/16/16.

The trailhead resides near the boundary of three states: Kentucky, Tennessee and Virginia. For this reason, it is sometimes difficult to discern what state you are in.

From the Visitor Center in Middlesboro, just off US-25E, drive approximately four miles up Pinnacle Road (A.K.A. Skyland Road). It is very steep, but well-maintained. It dead-ends at a small parking lot.

A stone-work landing with interpretive signs and restrooms greet visitors near the parking lot. Above the landing, a sign is posted for Ridge Trail.



Ridge Trail runs along Cumberland Mountain for the length of the park, about 19 miles. This article will only discuss the first 1.7-mile segment from Pinnacle Overlook to its intersection with Lewis Hollow Trail.


On 10/15/16, I trekked to Lewis Hollow Trail, descended to Wilderness Road Campground, climbed back up the mountain then returned to Pinnacle Overlook – about 7.5 miles. The steep inclines made the hike brutal.

As its name implies, Ridge Trail follows the ridge of Cumberland Mountain. It is an up-and-down path that I consider moderately difficult, although I have only explored this first segment.

Gee thanks

Gee thanks 10/15/16

At high elevation, the forest is thin and airy, the wind sharp and the views considerable. I found one undeveloped overlook that I call Ridge Trail Overlook #1. I am not sure about its location; it is perhaps 0.75 miles from the Pinnacle.



Ridge Trail connects to numerous other trails. Remember that if you leave it, you will likely descend the mountain, which will greatly increase the difficultly of your hike.

As I wandered further from the tourist area of Pinnacle Overlook, I encountered fewer people. I then entered a wilderness braved mainly by advanced hikers, which I loved. I have often avoided places such as Red River Gorge and the Great Smokey Mountains because they are crowded. One of the great allures of the wilderness, for me, is being alone.

I needed solitude. I reflected about the end of a relationship. I asked myself: “At 38-years-old, am I equipped for relationships?” “Is there something wrong with me?” “Will I die alone?”

This led me to ponder about life and death. I examined the ancient geology of the mountain, which was like peering into a mirror of my own insignificance.

Long ago, Cumberland Mountain was nothing more than a bump beneath the sea. It rose slowly through sedimentation and tectonics. Time, water and wind now carve away at the dormant mountain. It will gradually erode into obscurity.

I will pass away too, but the earth will carry on. My triumphs and struggles will cease to exist even as a memory.

These lonely thoughts on the mountain are humbling; they put my diminutive problems in perspective. I am but a tear in a sea of time

I am nothing.


On 10/16/16, Robert, Shane and I hiked from the Pinnacle to Ridge Trail Overlook #1. A power-walking young lady passed us, wearing jogging pants and headphones. She appeared unarmed and unnerved. We shook our heads.

I cannot lecture against hiking solo because I take that risk so often myself, but the danger that the jogging lady brought upon herself was far worse. Without a firearm, she had no means to defend herself against three scraggly old men (thankfully, we were harmless). She was also defenseless in the unlikely event that an animal attacked her. Furthermore, she would have not heard its approach due to her headphones.

This is not the way to behave in a wilderness area. I hope that she does not learn this the hard way.

Added 10/21/16 – Updated 10/25/16