South of Lexington near Pineville in the Cumberland Gap National Historical Park, the 17 mile Ridge Trail straddles the crest of the Cumberland Mountains east of Cumberland Gap, starting at Pinnacle Overlook and leading hikers 16.6 miles to the parks eastern boundary, near White Rocks. Hardwood forests of hickory, oak, and maple cloak the precipitous mountainsides, interrupted by rocky outcrops that afford views of the high valleys below.
To reach the hiking trailhead from Lexington, head south and follow US 25 east into the park. The trailhead is at the end of Pinnacle Road.
Overall, Cumberland Gap National Park is the 1st most popular hiking trail of all 9 hikes in Kentucky.