Trail Running calendar near Chesterfield County 2026-2027

Experience the Night Owl 9K at Freedom Park featuring technical single track trails and rolling hills. Enjoy a post race party with pizza and live owls while supporting local wildlife rehabilitation.

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.

Experience a dog friendly trail race through the varied terrain of Caledon State Park. Run a 10K or 1 mile course with your leashed companion to support local natural resources and educational programming.

Experience a professional canicross and trail race on a beautiful horse rehabilitation campus in Virginia. Choose from competitive or casual distances and enjoy a festive atmosphere with food trucks and local vendors.

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.

Run scenic looped trails at Medoc Mountain State Park with single track, varied hills and a summit loop in 5 and 10 mile options. Limited to 500 runners, the race offers shirts, unique medals and hearty postrace soup and hot dogs.

Explore Wintergreen’s scenic Blue Ridge single track on a timed, non competitive trek with 7 to 28 mile options and 10 hours to finish. Enjoy rocky overlooks, a post trek party with food, finisher shirt and patches and medal opportunities.

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..

Experience a timed trail challenge at Windsor Castle Park with 8 hour and 4 hour options or a scenic 10K. Run or ruck a 5 km loop through beautiful nature and enjoy a fully stocked ultra style aid station.

Run a scenic and flat half marathon on the historic Dahlgren Railroad Heritage Trail in Virginia. This out and back course features a smooth railroad bed, custom medals, and a community atmosphere with post race refreshments.

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..