Trails in Middlesboro, Kentucky

Explore 2 scenic hiking trails across 1 mile (2 km) in Middlesboro, Kentucky.

Default image for Pinnacle Overlook Trail, a 0.2-mile trail in Middlesboro, KY (US)

0.2 Miles
0.3 km

Easy Out-and-Back

Pinnacle Overlook Trail

Cumberland Gap National Historical Park, Kentucky

Created By:

David Miller (Admin)

Default image for Pinnacle Overlook Loop Trail, a 0.4-mile trail in Middlesboro, KY (US)

0.4 Miles
0.6 km

Easy Loop

Pinnacle Overlook Loop Trail

Cumberland Gap National Historical Park, Kentucky

Created By:

David Miller (Admin)

Trails by Category

Colorado's Million Dollar Highway

Plan a day's drive adventure along the iconic Million Dollar Highway in Colorado. Explore the best short trails, roadside stops, waterfalls, vistas, ghost towns, and hot springs within a ~6 hour road trip.

Read

Explore

Glacier's Going-to-the-Sun Road

Discover the breathtaking beauty of Glacier National Park along the iconic Going-to-the-Sun Road. From stunning roadside stops to picturesque waterfalls and vistas, this engineering marvel offers endless opportunities for exploration.

Read

Explore

New York's Best Waterfalls

Whether you're planning a day hike, roadside stop, or a leisurely short walk, this guide provides hikers, travelers, and locals alike with 63 different locations to over 100 scenic waterfalls to help plan your next adventure!