Trail Running calendar near Williamsburg 2026-2027

Enjoy a fast, scenic half marathon along the flat Dahlgren Railroad Heritage Trail in King George, VA on Jan 31, 2026. Cupless racing with SpeedCup options, aid stations, and a custom finisher medal support the local trail.

Take on the Swammie Shuffle 200, a more than 200 mile self supported coastal ultra starting at Sandbridge with 5.5 days to finish, passing lighthouses and Corolla wild horses. Limited spots and proceeds benefit veterans.

Discover scenic trails around Saint Marys Lake near Leonardtown, MD with 17K, 34K or 50K on one to three laps through Salem Forest. Limited to 100 runners, this intimate event has rugged single track, lake views and on course aid.

Run Blackbeard's Revenge 100 Ultra and Relay across the scenic Outer Banks from Corolla to Hatteras with solo and relay entries on a paved coastal route. Expect aid stations, a finisher medal or 100 mile buckle and a finish at The Wreck.

Experience the Women's Trail Festival in Williamsburg, a two day event with technical 10 mile and 8k trail options for racers or hikers. Enjoy clinics, classes, a finisher medal and community giving that supports local charities.

Relaxed 14 mile point to point run along the scenic Dahlgren Railroad Heritage Trail in Virginia with gentle elevation. Quirky aid stations serve pie, s'mores and pretzels and finishers receive practical swag while supporting local charitie..

Run the scenic Long Creek 60K or 30K at First Landing State Park in Virginia Beach through maritime forest, cypress swamp and beach shoreline. The 30K is one loop, the 60K two loops, with aid stations and a reusable SpeedCup.

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.

Take on the Taskinas Creek Half Marathon at York River State Park, a trail friendly 13.1 mile hike or run with rolling single track and a tough final two miles. Limited to 250 entries, medals and PR coaster awards await finishers.

Run loops around scenic Windsor Castle Park in Smithfield, VA with timed options from a one lap 5k up to 10 hours. Rucking is welcome for the longer events and a stocked aid station plus homemade finisher items make this a low key, supporti..

Run through Creekside Farm on scenic dirt trails along the Rappahannock River with 5K and 8K options, chip timing and awards. Celebrate after with live music, craft beer, a free pint for entrants 21 plus and food trucks.

Run with your dog at the Howlin' Coyote Canicross Trail Race in Caledon State Park, featuring varied terrain and a 10 km canicross plus a one mile Wild Pup dash. This non profit event supports Friends of Caledon and is disposable cup free.

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.

Get Outside 8 Hour at Windsor Castle Park offers solo and team options on a scenic 5K loop with timed formats from 8 hours to 5K. Ruck entries carry 10 pound packs, the course is chip timed, and all finishers get a homemade medal.

Run a scenic 50K two loop course at First Landing State Park in Virginia Beach on December 13, 2026, with aid stations and a lively finish. Finishers get a Brooks shirt and medal and can celebrate at a brewery party.