About trails in Monroe County, Florida

Monroe County has 69 named trails on the map, covering 286 miles in total, an average of 4.1 miles per trail. That is the 17th largest mapped trail network among 61 counties in Florida. 38 of them are tagged for hiking and 14 for mountain biking.

The longest single trail is Florida Keys Overseas Heritage Trail, at 171 miles. 3 trails run 5 miles or longer. Mapped points of interest in the county include 4 trailheads, 115 campsites, and 97 boat launches. The nearest towns to these trails are Layton, Big Pine Key, and Cudjoe Key.

What the trails in Monroe County are like

By length, 35 are under a mile, 13 run 1 to 5 miles, and 3 are 5 miles or longer. 8 are loops, ending where they start; the longest is Coastal Prairie Trail, at 12.4 miles.

Every one carries a difficulty rating: 51 easy. Of the 51 with measured elevation, Florida Keys Overseas Heritage Trail climbs the most, about 173 ft.

Explore by activity

286Total miles

115Campsites

97Boat launches

4Trailheads

Florida Keys Overseas Heritage TrailMTB171 mi Coastal Prairie TrailHike12.4 mi Rowdy Bend TrailHike5.2 mi Snake Bight TrailHike3.7 mi Bear Lake TrailHike3.6 mi Christian Point TrailHike3.6 mi Crosstown GreenwayMTB3.2 mi Pace's Dike TrailHike3.1 mi Loop RoadHike3.0 mi Flagler AvenueMTB2.0 mi Bear Lake Hiking TrailHike1.8 mi Bear Lake RoadHike1.8 mi Port Bougainville TrailHike1.8 mi Guy Bradley TrailHike1.1 mi Mangrove TrailHike1.1 mi Golden Orb TrailHike1.1 mi Truman AvenueMTB0.9 mi Simonton StreetMTB0.8 mi Watson TrailHike0.7 mi Southard StreetMTB0.7 mi Old Seven Mile BridgeHikeMTB0.7 mi Bayshore Loop TrailHike0.6 mi Fleming StreetMTB0.6 mi Hammock TrailHike0.6 mi United StreetMTB0.6 mi Fogarty LaneHike0.5 mi Eco PondHike0.5 mi Eco Pond TrailHike0.5 mi Northside DriveMTB0.4 mi 14th StreetMTB0.4 mi 1st StreetMTB0.4 mi Bertha StreetMTB0.4 mi Pruitt DriveHike0.3 mi Henry Morgan RoadHike0.3 mi 5th StreetHike0.3 mi Wild Tamarind TrailHike0.3 mi Bachmann RoadHike0.3 mi Old State RoadHike0.3 mi Caroline StreetMTB0.3 mi Grove TrailHike0.3 mi Shoreline RoadHike0.2 mi Flagler Quarry TrailHike0.2 mi Windley TrailHike0.2 mi Old Bahia Honda Bridge TrailHike0.2 mi Tree Snail Hammock TrailHike0.2 mi Quarry Wall WalkHike0.1 mi Mannillo TrailHike0.1 mi Silver Palm Nature TrailHike0.1 mi Quarry Station TrailHike0.1 mi Gilbert's ResortHike0.1 mi Park DriveHike0.1 mi

Trails by town in Monroe County

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Trail geometry from OpenStreetMap contributors, licensed ODbL. Elevation from the USGS 3D Elevation Program. Compiled and published by Trailmonger · trail data last rebuilt October 25, 2026.