Trail Running calendar near Midlothian 2025-2026

The Happy Tail Wine Trail 5k is a virtual running event benefiting the Louisa Humane Society in Louisa, Virginia. Traditionally held at 53rd Winery, the course features a scenic, mostly flat cross-country route around vineyards and winery grounds. The event includes a 5k run, a 1-mile fun run for ch..

The Taskinas Creek Half Marathon is a mostly trail-based race held at York River State Park in Williamsburg, Virginia. The course features a mix of single track mountain bike trails, fire road trails, and about one mile of pavement, with rolling terrain and approximately 600 feet of elevation gain...

The National Trails Day 5K in Rice, Virginia, is a celebration of outdoor activity and community spirit, taking place at High Bridge Trail State Park. This event features a scenic out-and-back course across the historic High Bridge, designed for both runners and walkers. Participants can enjoy the c..

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 distances: a 50K, a half marathon, and a sunset 5K, all following a historic rail trail through scenic countryside and small towns. Th..

The OSS/CIA 50 Mile Night Run is a challenging ultramarathon held in Prince William Forest Park, Virginia, known for its historical ties to the U.S. intelligence community. The race features a 50-mile course primarily on single-track trails, with some fire roads and crossings, run twice to complete..

The High Bridge Challenge is a multi-distance trail running event held at High Bridge Trail State Park in Virginia. Participants can choose from various race options, including 26K, marathon, 100K, and 150K, with the opportunity to complete combined "train" races in June and December for special awa..

The Last Stand Army Backyard Ultra is a challenging endurance race held in Midlothian, Virginia, on Flag Day, June 14, 2025, to honor the 250th Birthday of the U.S. Army. Participants run a 4.167-mile loop every hour on the hour, continuing until only one runner remains to complete a final loop.The..

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, offering a mountain bike trail-like experience. The ra..

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 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 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 featuring dirt, gravel, grass, and pine needle surfaces. The course offers nearly 100% shade from surrounding trees, prov..

The Dahlgren Heritage Rail Trail 50K is a challenging ultramarathon held in King George, Virginia, on the scenic Dahlgren Railroad Heritage Trail. This flat, well-maintained, and mostly shaded out-and-back course spans 31 miles along a converted railroad bed featuring dirt, grass, pine needles, crus..

The Jarmans Invitational Marathon, held annually in Crozet, Virginia, is a challenging 30-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 and descent. The course is know..

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 Terrible Twelve is a 12-hour self-supported trail running event held at the Warhill Nature Trail in Williamsburg, Virginia. Participants run or walk as many 3.7-mile loops as possible on a crushed gravel course featuring rolling hills and scenic views, though personal lighting is required for ni..

The Orchard Dash 10k is a cross-country trail race held at Albemarle CiderWorks in North Garden, Virginia. The event features both 5k and 10k routes, with the 10k consisting of two laps on a hilly course. Participants receive a finisher’s medal, a technical event shirt, and a glass of cider from Alb..

The 12 Hour - Adventure Trail Run is an endurance event held at Prince William Forest Park near Triangle, VA. Participants run on a 6.5-mile looped trail course featuring single track, fire roads, and varied terrain with hills, rocks, roots, and mud. The event challenges both novice and experienced..

The Pawpaw 10 Miler and 5 Miler take place at Powhatan State Park in Powhatan, Virginia, celebrating the park's 10th anniversary alongside the annual Pawpaw Festival. The event offers a 10-mile race and a shorter 5-mile option, featuring scenic routes along the James River, open fields, shaded singl..

The Brandy Station Battlefield 10k is a trail running event held at Brandy Station Battlefield in Virginia. The course combines cross country terrain with gravel dirt roads, featuring slight elevation changes but no major climbs. Runners can choose between 5k and 10k distances, with the 10k route be..

The Fox Trot 5k in Keswick is a scenic cross-country race held at Merrie Mill Farm & Vineyard. The event features a 5k course that loops once around the winery property, including a mix of flat gravel, dirt, paved roads, and some notable hills. A 1-mile race option is also available.Participants rec..