About hiking in Chesapeake city

Chesapeake city, Virginia has 37 named trails tagged for hiking, covering 68.3 miles, an average of 1.8 miles each. The longest is East Ditch Trail, at 13.2 miles. 3 run 5 miles or longer.

All 37 hiking trails, longest first

East Ditch TrailHike13.2 mi Big Entry Ditch RoadHikeMTB5.1 mi Big Entry Ditch TrailHike5.1 mi East Ditch RoadHikeMTB4.5 mi Portsmouth Ditch RoadHikeMTB4.1 mi Portsmouth Ditch TrailHike4.1 mi Camp Ditch TrailHikeMTB3.9 mi Western Branch TrailHikeMTB3.0 mi Northeast Ditch RoadHikeMTB2.5 mi Northeast Ditch TrailHike2.5 mi Rosemary Ditch TrailHike2.3 mi Black Bear TrailHike2.2 mi Western Branch Park Walking TrailHike2.0 mi Indian Creek TrailHike1.9 mi Rosemary Ditch RoadHikeMTB1.3 mi Molly Mitchell TrailHike1.3 mi Shuttle TrailHike1.1 mi Fresian Horse TrailHike1.1 mi Central LoopHike1.0 mi Deer Island TrailHike0.8 mi Otter Point TrailHike0.7 mi boundary pathHike0.7 mi Paint Horse TrailHike0.6 mi South LoopHike0.5 mi Quarter Horse TrailHike0.4 mi Paso Fino Horse TrailHike0.4 mi North LoopHike0.4 mi Spotted Horse TrailHike0.4 mi Main TrailHike0.3 mi walking pathHike0.2 mi Molly Mitchell Accessible TrailHike0.2 mi Right Hook TrailHike0.2 mi Entrance 4Hike0.1 mi Stewartia TrailHike0.1 mi Cutthroat TrailHike0.1 mi Arabian Horse TrailHike0.1 mi Osprey TrailHike0.1 mi

← All Chesapeake city trails

Trail geometry from OpenStreetMap contributors, licensed ODbL. Elevation from the USGS 3D Elevation Program. Compiled and published by Trailmonger · trail data last rebuilt August 9, 2026.