About hiking in Madison County

Madison County, Kentucky has 39 named trails tagged for hiking, covering 37.2 miles, an average of 1.0 mile each. The longest is 3. Cowbell Hollow Loop (green, 2.9mi), at 2.8 miles.

What the hiking trails in Madison County are like

By length, 23 are under a mile and 16 run 1 to 5 miles. 4 are loops, ending where they start; the longest is Bluegrass Overlook Trail, at 2.2 miles.

Of the 39 with measured elevation, 3. Cowbell Hollow Loop (green, 2.9mi) climbs the most, about 1,828 ft, and 2 gain 1,000 ft or more.

All 39 hiking trails, longest first

3. Cowbell Hollow Loop (green, 2.9mi)Hike2.8 mi West Barton TrailHike2.7 mi 1. Pinnacle Knob Trail (blue, 2.7mi)Hike2.6 mi Bluegrass Overlook TrailHike2.2 mi Lower Pinnacle TrailHike1.9 mi Robe Mountain TrailHike1.5 mi Kelly’s TrailHike1.4 mi Tudor Farm TrailHike1.4 mi Upper Pinnacle TrailHike1.3 mi Berea City Park TrailHike1.3 mi Upper Hines trailHike1.1 mi blueHike1.1 mi East Pinnacle TrailHike1.1 mi greenHike1.1 mi John B Stephenson Memorial TrailHikeMTB1.0 mi 2. Pigg Hollow Loop (red, 1.0mi)Hike1.0 mi Cross Country TrailHike0.9 mi redHike0.9 mi yellowHike0.8 mi West Pinnacle TrailHike0.8 mi Indian Fort PathHikeMTB0.8 mi Lake Reba walking trailHike0.7 mi Berea Municipal LoopHikeMTB0.6 mi Walnut TrailHike0.6 mi Learn & Burn TrailHike0.5 mi Prescribed Burn Interpretive TrailHike0.5 mi Davis Hollow TrailHike0.5 mi Upper West Pinnacle TrailHike0.5 mi Old Daniel Boone RoadHike0.4 mi Buzzard's Roost TrailHike0.4 mi Upper East Pinnacle TrailHike0.3 mi Rock House TrailHike0.3 mi 4. Chestnut Loop (yellow, 0.3mi)Hike0.3 mi Duncannon Walking TrailHike0.3 mi JaneHikeMTB0.3 mi blackHike0.2 mi Berea College cross-country running trailHike0.2 mi whiteHike0.2 mi Eagle's Nest TrailHike0.2 mi

← All Madison County trails

Trail geometry from OpenStreetMap contributors, licensed ODbL. Elevation from the USGS 3D Elevation Program. Compiled and published by Trailmonger · trail data last rebuilt October 4, 2026.