About trails in Greater Bridgeport Planning Region, Connecticut

Greater Bridgeport Planning Region has 57 named trails on the map, covering 88.5 miles in total, an average of 1.6 miles per trail. That is the 9th largest mapped trail network among 9 counties in Connecticut. 53 of them are tagged for hiking and 4 for mountain biking.

The longest single trail is hiking, at 41.2 miles. 2 trails run 5 miles or longer. Mapped points of interest in the county include 2 trailheads, 4 campsites, 2 waterfalls, and 20 boat launches. The nearest towns to these trails are Stepney, Bridgeport, and Murray.

What the trails in Greater Bridgeport Planning Region are like

By length, 48 are under a mile, 7 run 1 to 5 miles, and 2 are 5 miles or longer. 2 are loops, ending where they start; the longest is Dear Meadow Loop, at 0.8 miles.

Of the 57 with measured elevation, hiking climbs the most, about 1,754 ft.

Explore by activity

89Total miles

4Campsites

20Boat launches

2Waterfalls

2Trailheads

hikingHike41.2 mi Pequonnock River TrailMTB16.7 mi Stepney Rail TrailMTB4.2 mi Ordway TrailHike1.9 mi Pink Trail (Off Leash Loop)Hike1.7 mi Randall's Farm Preserve TrailHike1.5 mi Yellow TrailHike1.5 mi Newtown Rail TrailMTB1.4 mi Housatonic Avenue BikewayMTB1.1 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 AvenueHike0.1 mi Walsh wetlandsHike0.1 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

Trails by town in Greater Bridgeport Planning Region

More Connecticut counties

Southeastern Connecticut Planning Region

169 trails · 238 mi

Western Connecticut Planning Region

262 trails · 458 mi

Capitol Planning Region

490 trails · 1,117 mi

Lower Connecticut River Valley Planning Region

206 trails · 499 mi

Naugatuck Valley Planning Region

159 trails · 290 mi

Northeastern Connecticut Planning Region

138 trails · 301 mi

Northwest Hills Planning Region

243 trails · 556 mi

South Central Connecticut Planning Region

243 trails · 524 mi

← All of Connecticut

Trail geometry from OpenStreetMap contributors, licensed ODbL. Elevation from the USGS 3D Elevation Program. Compiled and published by Trailmonger · trail data last rebuilt September 24, 2026.