Virginia Capital Trail
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.
Roadbike loop from Nimmo
55.1 km40 mElizabeth River Trail and Ocean View Loop
46.8 km49 mVirginia Beach and First Landing State Park loop
45.0 km52 mSouthern Tip Bike & Hike Trail
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
Ride Chesapeake at the right time
Compare routes in Chesapeake, choose a departure window that matches the forecast, and navigate with confidence. With Tailwind GPS you get route planning, wind-aware scoring, and turn-by-turn guidance in one place — built to help cyclists find their best ever ride.