The Pinnacle Trail accesses the Pinnacle overlook at Cumberland Gap. From the trailhead along KY 988 in Kentucky, proceed 1.6 miles along the Harlan Road Trail which ascends at a brisk but manageable pace to the Pinnacle Road. At Fort McCook, which was occupied by both the Confederate and the Union during the Civil War, turn towards the Pinnacle Trail that ascends steeply for .8 of a mile to the Pinnacle Overlook — at 2,440 feet in elevation. There are various viewpoints from the Pinnacle, so be sure to take it all in!
Proceed eastward from the overlook along a paved path towards Fort Lyon, which was also occupied during the Civil War for only a brief time. Another overlook, albeit not as spectacular as the Pinnacle, is just ahead. A trail departs near the second overlook for the Ridge Trail; follow the spine of the Cumberland Mountains for 1.8 miles. It is a wide path, a remnant of a former dirt road. Turn left at the junction with the Sugar Run Trail, which is a beautiful hike to the base of the mountain, following Sugar Run for much of its length. Take the left fork near the base to the Harlan Road Trail parking lot.
The trail is 6.8-miles in length. The trailhead is along KY 988, which departs from the Visitors Center towards Sugar Run at Harlan Road.
- Location: Cumberland Gap
- Trail Number:
- Length: 6.8 miles
- Difficulty: 2 – Moderate
- Condition: 1 – Good
- Scenery: 1 – Exceptional