About hiking in Greater Bridgeport Planning Region

Greater Bridgeport Planning Region, Connecticut has 53 named trails tagged for hiking, covering 65.2 miles, an average of 1.2 miles each. The longest is hiking, at 41.2 miles. 1 runs 5 miles or longer.

What the hiking trails in Greater Bridgeport Planning Region are like

By length, 48 are under a mile, 4 run 1 to 5 miles, and 1 is 5 miles or longer. 2 are loops, ending where they start; the longest is Dear Meadow Loop, at 0.8 miles.

Of the 53 with measured elevation, hiking climbs the most, about 2,282 ft.

All 53 hiking trails, longest first

hikingHike41.2 mi Ordway TrailHike1.9 mi Pink Trail (Off Leash Loop)Hike1.7 mi Randall's Farm Preserve TrailHike1.5 mi Yellow TrailHike1.5 mi Seven Ponds TrailHike1.0 mi Oak Hill TrailHike0.9 mi Great Hollow Lake LoopHike0.8 mi Ruth’s TrailHike0.8 mi Dear Meadow LoopHike0.8 mi Edna Strub Chiboucas Special Use TrailHike0.7 mi Wolfe Park - Great Hollow LakeHike0.7 mi "Pog Trail"Hike0.6 mi Paine Barn TrailHike0.6 mi White TrailHike0.6 mi Saint Mary's by the seaHike0.6 mi Dirty Swamp TrailHike0.5 mi Country LaneHike0.5 mi Paul Busch TrailHike0.5 mi BlueHike0.5 mi Putnam Preserve TrailHike0.5 mi Norton RoadHike0.5 mi Laurel Ledges TrailHike0.4 mi Maple Road TrailHike0.4 mi Saint Timothy's LoopHike0.3 mi Chipmunk RunHike0.3 mi Serenity LoopHike0.3 mi Patchau TrailHike0.3 mi Muskrat HollowHike0.3 mi Cattail TrailHike0.3 mi West Woods TrailHike0.3 mi Ox Cart TrailHike0.2 mi Reverse Jug Handle/Jug HandleHike0.2 mi Great Meadows TrailHike0.2 mi Apple Tree Crossing TrailHike0.2 mi Sturges Pond TrailHike0.2 mi Long Beach StreetHike0.2 mi Ash Creek PathHike0.2 mi Rock Ledge TrailHike0.2 mi Dear Meadow TrailHike0.2 mi Fragrance LoopHike0.2 mi Azalea TrailHike0.2 mi Pond TrailHike0.2 mi University AvenueHike0.2 mi Walsh wetlandsHike0.2 mi Wetland TrailHike0.1 mi Streamside TrailHike0.1 mi Trillium TrailHike0.1 mi Cottontail CutoffHike0.1 mi Evergreen TrailHike0.1 mi Nash TrailHike0.1 mi Aspetuck Blue TrailHike0.1 mi Aspetuck Red TrailHike0.1 mi

← All Greater Bridgeport Planning Region 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.