Trail Running calendar near Williamsburg 2026-2027

An out-and-back ultramarathon of more than 200 miles from Sandbridge Beach through the Outer Banks to Cape Hatteras Lighthouse. The event raises funds for veteran suicide prevention with all proceeds split between Awareness N Action and Mis..

Trail races near Leonardtown, MD on an ~10.5 mile loop around a 250 acre lake, offered as 17K, 34K, or 50K with two aid stations and a 100 runner limit.

A point to point ultra on the Outer Banks from Corolla to Hatteras with 100% paved coastal roads. Events include 100 mile, 100K, relay, virtual options and pacer roles, finishing at The Wreck Tiki Bar.

A 5K trail event at Chanco on the James in Surry County offering run, walk, and hike options along woods and the James River; online registration closes March 19 and race day registration is available.

A two-day women's trail festival in Williamsburg, VA with a competitive ten mile trail run plus an 8k and noncompetitive hikes, talks, and exercise classes. Proceeds support local charities and all finishers receive a medal and a T shirt.

A 14-mile untimed point to point trail run in King George, Virginia following the Dahlgren Railroad Heritage Trail. The cupless event features themed aid stations, shuttle service, practical finish swag and supports Sheetz For the Kidz.

A 5K run and walk at Appomattox River Regional Park in N. Prince George on April 11, 2026. All participants receive a medal and awards will recognize top overall and age group finishers; early registrants receive T shirts while sizes last.

Trail ultramarathon through nine trails in First Landing State Park, featuring marsh, forest, bay shoreline and a beach segment. Both 60K and 30K are cupless and include three aid stations and a 200 ml collapsible cup at pickup.

Four teams of eight runners will complete a 122.4 mile relay at Pocahontas State Park on April 24 and 25, 2026, with proceeds supporting Kids On The Move, a Sports Backers youth running program.

Run for a cause on the scenic Virginia Capital Trail at the Motion for Justice 5K. This flat, paved course offers views of the James River and includes chip timing, a finisher medal, and a tech shirt. Awards recognize top overall and age gr..

On May 16, 2026 at Bells Mill Park in Chesapeake the Strider XC Classic features a 5K cross country race, a competitive 5K race walk, and a 1.5 mile kids race, with one aid station, shirts for the first 150 registrants, and medals for all f..

A mostly trail half marathon at York River State Park with a new no frills Hike a Half format. The route mixes single track, fire road and a short paved section, includes aid stations and limited entries for a smaller field.

Run for up to 10 hours on a 3.1-mile trail loop in Windsor Castle Park. Choose from shorter timed races or try the rucking option. All finishers get a handmade medal and there are awards for the top performers.

Run a scenic 5K or 8K on the trails of Creekside Farm Brewery in King George. Enjoy a post-race party with live music, a complimentary craft beer, and local food trucks. All participants get an event shirt and a souvenir pint glass.

Run with your dog at the Howlin' Coyote Canicross Trail Race in King George, Virginia. Choose between a 10K or a 1 mile event on varied terrain. Your entry supports the Friends of Caledon State Park.

Pocahontas Trail Festival at Pocahontas State Park on October 4, 2026 offers a Half Marathon and a 10k on redesigned trail loops with chipped timing. Water stations are near miles 3, 6 and 9 and awards are given by age group.

A 50K race and team relay on the Noland Trail at The Mariners' Museum Park in Newport News on November 7, 2026. The course is six laps and relay teams of two to six share the distance; participants also gain access to the fall festival.

A low-key trail event at Windsor Castle Park with 8-hour, 4-hour, and 10K options. Run or walk a marked 5-km loop with a stocked aid station, or try the rucking division. All finishers get a homemade medal, with awards for top performers.

A two-loop 50K trail run through First Landing State Park. Runners navigate a cupless course with two aid stations and an 8-hour time limit. All finishers get a medal, and a post-race party with pizza and drinks awaits.