Trail Running calendar near Chesterfield 2026-2027

Event Information The High Bridge Challenge involves completing a combination of distances from two separate running events: the Freight Train in May and the Night Train in June. Both events take place on the High Bridge Trail in High Bridg..

The Night Owl 9K will take place in Williamsburg on Saturday 27 June 2026. You can run 9 kilometers.

Test your endurance at Windsor Castle Park with timed races ranging from two to ten hours on a scenic trail loop. This manually timed event features a support station and options for both runners and ruckers.

A cross-country 5k and 10k at Albemarle CiderWorks featuring chip timing, a finisher medal, technical shirt and a glass of cider; proceeds support Rikki's Refuge.

Run through a scenic 1000 acre farm bordering the Rappahannock River followed by live music and craft beer at Creekside Farm Brewery. Enjoy chip timed 5K or 8K trail courses with custom swag and local food trucks.

Run or hike the scenic trails of Powhatan State Park along the James River. This event celebrates the native pawpaw fruit with a festival featuring live music. It's a benefit for the Friends of Powhatan State Park.

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.

Take on a trail run through Walnut Creek Park with both 5k and 10k options. Your participation supports Rikki's Refuge, and you'll earn points in the organizer's annual race series. Runners receive a tech shirt, finisher's medal, and chip t..

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.

The Dahlgren Trail Half Marathon will take place in King George on Saturday 16 January 2027. You can run 21 kilometers.

Holiday Lake offers 10K, 25K, and 50K distances on a scenic loop around the lake in Appomattox, Virginia. The 50K is known as a classic first ultra and kicks off the Lynchburg Ultra Series. Weather can range from pleasant sun to snowy winte..