Trail Running calendar near Chesapeake 2025-2026

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 challenge with on course aid and a Brooks shirt for registrants. Celebrate with a medal and a post race party at Smartmouth Br..

Tackle a scenic 10 mile trail run at York River State Park featuring technical single track, fire roads and a downhill finish. Proceeds benefit AWARE and you can meet owls onsite while enjoying coffee and snacks after the run.

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.

Run scenic trails at Harwoods Mill Park in Yorktown, VA on January 17, 2026 with a Half Marathon or 5K option. Limited fields, aid stations, and post race shirts make this a chilly January favorite for trail lovers.

Take on the Swammie Shuffle 200, a 200+ mile self supported out and back along beaches and the Outer Banks, with 5.5 days to finish. Run to support veteran suicide prevention, benefiting Awareness N Action and Mission22.

Experience the Outer Banks in Blackbeard’s Revenge 100 Ultra & Relay, a point to point coastal run from Corolla to Hatteras. Choose 100 mile, 100K, or a 100 mile relay and tackle scenic shorelines and variable OBX weather.

Join the Women's Trail Festival, a two day trail weekend at Freedom Park in Williamsburg with 10 mile and 8k options plus social hours and educational talks. All finishers earn a medal, proceeds benefit local charities and the event is Trai..

Choose a 60K (two loops) or 30K at First Landing State Park in Virginia Beach and run scenic trails, marsh and shore. Aid stations support you and finishers receive a custom award.

Run or hike the Taskinas Creek Half at York River State Park on June 7, 2026. This no frills trail event features rolling, rugged terrain and is limited to 250 entrants, with finisher medals and a special PR award for faster finishers.

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..

Take on scenic new trails at Pocahontas State Park with a chip timed half marathon or 10K. Expect runnable singletrack, on course water stations, live results and race day age group awards in a festive park setting.

Run five hourly 5K loops for a cumulative 25K at Jockey's Ridge State Park, including a dune crossing and team relay options. Chip timing, finisher medal and a festival vibe with food, music and beach access make this a fun fall challenge.