Trail Running calendar near Chesterfield 2025-2026

The Taskinas Creek Half Marathon is a mostly trail-based race held at York River State Park in Williamsburg, Virginia. Limited to 150 runners, this low-key event features a challenging course with over half single-track mountain bike trails, dirt fire roads, and about one mile of pavement. The race..

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 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 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 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 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 flat, well-maintained, and mostly shaded converted railroad bed featuring dirt, grass, pine needles, crushed..

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 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 One Mile With a Smile 12 Hour Endurance Run takes place at Oak Grove Lake Park in Chesapeake, Virginia. Participants run multiple laps of a 1.5-mile loop over 12 hours, allowing runners to cover as much or as little distance as they choose. The course is flat, unpaved, and tree-lined, offering s..

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 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 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..

The Rehab Rover Canicross and Trail Race is an exciting event taking place in Gordonsville, Virginia, featuring a 10K, 5K, a casual dog-friendly 5K, and a virtual 5K option. Scheduled for October 4, 2025, this race promotes the bond between participants and their dogs as they navigate scenic trails..

The Pocahontas Trail Festival is a running event taking place at Pocahontas State Park in Chesterfield, Virginia. Scheduled for October 5, 2025, the festival features a Half Marathon and a 10k race, both designed to showcase the park's scenic trails. Participants will enjoy professionally timed race..

The Piedmont 8 Hour is a trail running event held at Powhatan State Park in Powhatan, Virginia. Celebrating its 10th year, the race features a 2.7-mile loop with about 60 feet of elevation change, winding through open meadows and pine forests with scenic fall foliage. The course is mostly runnable w..

The Wilderness Run 10k is a scenic cross-country race held at Wilderness Run Vineyard near the historic Chancellorsville and Wilderness battlefields. The event features both 5k and 10k courses with hills and trail terrain, offering a challenging and picturesque experience. Participants receive a fin..