Trail Running Calendar Virginia 2025-2026

The Last Stand Army Backyard Ultra, held in Midlothian, Virginia, is a unique endurance event honoring the 250th birthday of the U.S. Army. Participants run a 4.167-mile loop every hour, on the hour, with only one hour to complete each lap.The race continues until a single runner remains, testing me..

The Jackson River Scenic Trail Marathon, Half Marathon, 10k, and 5k is a vibrant running event taking place in Covington, Virginia. The USATF certified course starts and ends at the Intervale Trail Head, following a scenic route along the Jackson River. Participants can enjoy a smooth, mostly flat t..

The OSS/CIA 50 Mile Night Run is a challenging ultramarathon held in Prince William Forest Park, Triangle, Virginia, a historic site once used to train OSS spies during World War II. The event features a 50-mile race consisting of two laps on a 25+ mile loop primarily on single-track trails, fire ro..

The Night Train 50K and Half Marathon is an annual nighttime trail running event held at High Bridge Trail State Park in Farmville, Virginia. The race features three main distances: a 50K, a half marathon, and a sunset 5K, all following a historic rail trail through scenic countryside and small town..

The High Bridge Challenge in Farmville, Virginia, offers runners a unique opportunity to complete two races on the scenic High Bridge Trail State Park. Participants can choose from combo distances ranging from 26k to 150k, combining the Night Train race in June and the Freight Train race in December..

The Froggy Mountain 100 is an ultramarathon held in Galax, Virginia, featuring 50- and 100-mile race options on a challenging 1.1-mile loop course with approximately 500 feet of vertical gain per loop. The event takes place entirely on private property and offers aid stations with hot food at the st..

The Night Owl 9K is a challenging trail race held at Freedom Park in Williamsburg, Virginia. The 9-kilometer course features a mix of single track, fire road, and paved trails with rolling hills and technical sections including roots and twists, ideal for runners familiar with mountain bike-style tr..

The Hybrid 8K is a unique running event held in Danville, Virginia, that combines both trail and road running for an exciting race experience. Participants start at Anglers Park, running 2.5 miles on the Withcback trail through the woods, followed by a 2.5-mile finish on the road and the rolling Riv..

The 53rd Winery 5k & 10k is a scenic cross-country race held at 53rd Winery in Louisa, Virginia. Participants can choose between a 5k or 10k course, which loops around vineyards and winery grounds. The event features chip-timed races, finisher medals, technical shirts, and a complimentary glass of w..

The Leopold’s Preserve 10k is a trail running event held at Leopold’s Preserve in Broad Run, Virginia. Participants can enjoy a mostly flat dirt course with some roots, featuring scenic views of a diverse habitat and wildlife. The race is chip-timed and includes a finisher’s medal and technical even..

The 868 Estate Vineyards 10k and 5k is a scenic cross-country race held at 868 Estate Vineyards. Participants can choose between a 5k or 10k course around the vineyard property, featuring hills and beautiful views. The event includes a finisher medal, technical event shirt, and a glass of wine.Point..

The Hungry Mother Trail Run & Hike is an exciting outdoor event taking place at Hungry Mother State Park in Marion, Virginia. Scheduled for July 26, 2025, the event features multiple race options, including a 7k Summit Hike, a 7k Summit Race, an 8 Mile Race, and a challenging 25k Race. Participants..

The 3H Trail Half Marathon in King George, Virginia, is a scenic, flat, and fast out-and-back race held entirely on the Dahlgren Railroad Heritage Trail, a converted railroad bed offering solid footing with surfaces of dirt, gravel, grass, and pine needles. The course starts at the eastern end of th..

The Jarmans Invitational Marathon, held annually in Crozet, Virginia, is a challenging 29-mile race featuring a grueling course with 7,610 feet of elevation gain and loss. Runners tackle a steep gravel road, Jarmans Gap, five times, each lap involving a 2.9-mile climb with 1,522 feet of ascent. The..

The DHRT 50K is an exciting trail running event set in King George, Virginia, taking place on August 2, 2025. This challenging race traverses the scenic Dahlgren Railroad Heritage Trail, offering participants a flat and well-maintained course primarily shaded by trees. Runners will face the added ch..

The Dahlgren Heritage Rail Trail 50K is a challenging ultramarathon held in King George, Virginia, on August 2, 2025. This 31-mile race takes place on the Dahlgren Railroad Heritage Trail, a converted railroad bed featuring a flat, well-maintained, and mostly shaded course with surfaces including di..

The Merrie Mill Farm & Vineyard 10k is a scenic cross-country race held at Merrie Mill Farm & Vineyard in Keswick, Virginia. The course features a mix of flat gravel, dirt, and paved roads with some notable hills, offering one lap for the 5k and two laps for the 10k. Walkers are welcome, and a virtu..

The Crystal Springs Ultra Races take place in the scenic Crystal Springs Recreation Area in Wytheville, Virginia, featuring challenging trail runs on the High Rocks Spur and Boundary Trail loops. The event offers three distances: a 12.8-mile half marathon with 2,008 feet of elevation gain, a 25.6-mi..

The Third Winchester Battlefield Half, held on August 9, offers scenic trail routes through the historic battlefield. Participants can choose from a half marathon, 10k, or 5k race, with the half marathon consisting of three loops on a light gravel dirt path. The event features chip-timed results, fi..

The Flag Rock 5K Trail Run takes place in Norton, Virginia, within the scenic Flag Rock Recreation Area. This trail race is part of the High Knob Outdoor Fest, a weeklong celebration of non-motorized outdoor activities in the High Knob Region. The 5K course runs along the City of Norton's Flag Rock..