Virginia Capital trail loop
55.1 km80 m
Cycling routes / United States / Chesapeake
Best road cycling routes in Chesapeake
Here are curated road cycling routes in Chesapeake. Filter by distance and elevation to find your next ride.
Departure times are local to Chesapeake.
Nimmo road loop
55.1 km40 mElizabeth River trail loop
46.8 km49 mFirst Landing beach loop
45.0 km52 mSouthern Tip trail loop
45.9 km46 mBuild your own route
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How routes are ranked
Tailwind scores each route hour by hour using wind direction, weather, and a 25 km/h cycling pace. Routes are sorted by forecast score for your chosen departure time, highest first.
5 curated routes in Chesapeake, United States.
Nearby places
Plan and navigate rides in Chesapeake
Compare the best road cycling routes in Chesapeake, pick a departure time that fits the forecast, and open any ride on the map. Tailwind GPS is a free planning and navigation tool for cyclists: score routes hour by hour, download GPX files for Garmin, Wahoo, or any GPS device, build new loops in the route planner, and follow turn-by-turn guidance when it is time to ride.