Trail Running calendar near Chesapeake 2025-2026

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..

Celebrate the 30th Chesterfield Alumni Run on Thanksgiving at Pocahontas State Park with a free community XC 5k and kids fun run with gingerbread cookies. Stay for giveaways and optional donations to support local track and cross country.

Join the Tidewater Strider Dismal Swamp in Chesapeake VA on Dec 7, 2025 for 50K, marathon, half marathon, relays and a walkers option on scenic out and back looped trails. Aid stations, finisher apparel and post race pizza and beer await.

Run the Pocahontas 5k, 10k or half marathon on Dec 13 along the scenic Bright Hope Trail in Pocahontas State Park. Walkers and virtual runners welcome with chip timing. Finishers get a coin and shirt and proceeds benefit Operation Turbo.

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.

Run laps on a certified 3.75 mile loop through scenic Sandy Bottom Nature Park in Hampton, Virginia. Pick 8 hour or 4 hour timed options in a cupless format and earn a homemade medal for a friendly, rugged training day.

Enjoy The Chills in the Mill at Harwoods Mill Park in Yorktown with a scenic half marathon or upbeat 5K over mixed trail roads and single track. Small fields, on site awards and aid stations make this a welcoming winter race.

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.

Blackbeard's Revenge 100 is a point to point ultramarathon along North Carolina’s Outer Banks from Corolla to Hatteras, finishing at The Wreck Tiki Bar. Choose 100 mile, 100K, or relay entries and enjoy sweeping paved coastal views on March..

Run, learn and connect at the Women's Trail Festival in Williamsburg on March 28 and 29. Choose 10 mile or 8k routes, enjoy a shirt, lunch and finisher medal, and support local charities.

Run scenic trails at First Landing State Park in Virginia Beach with 30K and 60K options. Take in maritime forest, bay shoreline and beach views and earn a custom finisher award within the 10 hour time limit.

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..

Explore scenic new hiking trails at Pocahontas State Park with options of a half marathon or 10k, both starting and finishing on the park's grass field. Pro chip timing and live results add a competitive edge to this fall trail run.