Trail Running calendar near Chesapeake 2025-2026
We have found 17 Trailruns within 80 miles of Chesapeake. See below where and when you can find the races.
We have found 17 Trailruns within 80 miles of Chesapeake. See below where and when you can find the races.
Challenge yourself on the scenic Noland Trail with a 50K solo or join a team relay through Mariners' Museum Park, finishing to a festival of live music, craft beer and a custom finisher medal. Teams of 2 to 6 welcome.
Run through history in the Breakthrough Trail 5K at Pamplin Historical Park in Petersburg on November 1, 2025. This scenic run/walk threads historic battlefield trails over gravel and dirt, promising a memorable and rewarding finish at the..
Run the Mel Williams Memorial Seashore 50K at First Landing State Park in Virginia Beach, a scenic two loop trail with aid stations and a welcoming vibe. Registrants get a Brooks shirt, finishers a medal, and a post race brewery celebration..
Run the Snowy Owl 10 Mile at York River State Park near Williamsburg VA on January 4. This scenic trail race supports AWARE and features owls onsite, a finisher ceramic medal, and a cozy race hat for registrants.
Take on the Swammie Shuffle 200, a 200 mile ultramarathon along the Atlantic coast from Sandbridge to Cape Hatteras with lighthouses and wild Corolla horses. Proceeds support Awareness N Action and Mission22 to fight veteran suicide.
Join Virginia Run for Cancer in Hampton VA, a 24 hour solo and team event on a flat 3.75 mile dirt trail where runners and walkers of all abilities are welcome. Chase team and solo awards while supporting the American Cancer Society.
Run or hike the Taskinas Creek half marathon on June 7, 2026 at York River State Park in Williamsburg. Scenic trails and rolling hills, with a tough final two miles, make this relaxed Hike a Half a memorable challenge.
Windsor Castle Park hosts a low key, manually timed event on a shaded 3.1 mile loop in Smithfield, VA with 10 hour, 5 hour, 2 hour and 5k options. Stocked aid station, rucking option and handmade finisher items make for a friendly, challeng..