Trail Running calendar near Yorktown 2025-2026

Kick off the New Year with a no frills 5K or 8K along the Capital Trail in Williamsburg. Low cost entry supports CRR scholarship funds and the friendly post race vibe includes coffee and doughnuts.

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.

Take on the Sandy Bottom 8 hour Training Run at Sandy Bottom Nature Park, with timed or untimed options on a fast, flat 5 km loop through scenic trails. Bring your own hydration and enjoy homemade medals, swag, and a welcoming park vibe.

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.

The Delmarva Ultra Challenge is a 100K trail test in Pocomoke run as two 50K efforts, one night and one morning. A surprise night course and limited spots make this a gritty, tactical event for experienced ultrarunners.

Community driven 50K trail race through Pocomoke River State Park, featuring mostly flat single track and scenic river views. Volunteer run with stocked aid stations and a handmade ceramic mug for every finisher.

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.

Run a scenic 10.5 mile loop around Saint Marys Lake and into Salem Forest in Leonardtown, MD with 17K, 34K, and 50K options. Enjoy mostly single track trails, a field limited to 100 runners, and pancakes at the finish.

Explore a scenic 10 mile trail through laurel and pine in Pocomoke State Forest along Blades Road, with mossy singletrack and creek crossings. Bring your own cup or bottle as the race is cupless and offers one aid station.

Run coast to coast along North Carolina's Outer Banks from Corolla to Hatteras, enjoying fully paved roads and sweeping coastal views. Choose 100 mile, 100K, or a 100 mile relay and celebrate at The Wreck Tiki Bar finish.

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 a scenic, flat 5k along the Virginia Capital Trail by the James River at Rocketts Landing in Richmond. Choose in person or virtual entry, enjoy chip timing, a tech race shirt and finisher medal, with live results posted after the race.

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.

Pick your challenge on a scenic 3.1 mile loop at Windsor Castle Park with timed 10 hour, 5 hour and 2 hour options plus a one lap 5k and rucking available. Enjoy a low key vibe, a well stocked aid station and a homemade finisher medal.

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.