Trail Running calendar near Chesterfield 2025-2026

The 53rd Winery 5k & 10k is a scenic running event held at 53rd Winery in Louisa, Virginia. The course is a cross-country route looping around the vineyards and winery property, featuring a fairly flat terrain with some elevation changes. The 5k consists of three laps, while the 10k covers six laps...

The DHRT 50K is a challenging trail race held in King George, Virginia, along the Dahlgren Railroad Heritage Trail. This 50-kilometer event takes place in August, presenting runners with the added challenge of Virginia's intense summer heat and humidity. The course is fast and flat, mostly shaded by..

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

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 unique 12-hour endurance race held in Williamsburg, Virginia, on the Warhill Nature Trail. Participants run or walk as many 3.7-mile loops as possible from 7 PM to 7 AM, with a one-mile add-on available in the final half hour. The course features crushed gravel and rolling h..

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 them to run as much or as little as they choose. The course is flat, unpaved, and tree-lined, offering scenic views of..

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, featuring scenic runs along the James River, through open fields, shaded forests, and past historic cabin ruins. The event offers a 10-mile race and a shorter 5-mile option, both incorporating diverse terrain in..

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 includes a mix of flat gravel, dirt, paved roads, and some notable hills, offering a challenging yet picturesque run around the winery property. Participants can also ch..

The Pocahontas Trail Festival is a trail running event held at Pocahontas State Park in Chesterfield, Virginia. It features a Half Marathon and a 10k race, both starting and finishing on a large grass field near the park's boat launch. The course was redesigned to emphasize trail running, incorporat..

The Piedmont 8 Hour is an annual 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 ru..

The Wilderness Run 10k is a scenic cross-country trail race held at Wilderness Run Vineyard in Spotsylvania, Virginia, situated on historic Civil War battlefields. The course features rolling hills and consists of two laps of a 5k out-and-back route. Participants enjoy a vibrant atmosphere with post..

The Greensprings 24 is a 24-hour endurance race held in Williamsburg, VA, benefiting The Arc of Greater Williamsburg, a nonprofit supporting adults with disabilities. The race features a USATF-certified 2.215-mile loop course on mainly flat, scenic, crushed gravel trails with minimal elevation chang..

The Smithfield Hog Jog will take place in Smithfield on Saturday 25 October 2025. You can run between 5 and 5 kilometers.

The Noland Trail 50K & Relay is a unique running event held in Newport News, Virginia, within The Mariners’ Museum Park. Participants can choose to run solo or as part of a relay team of 2 to 6 members. The 50K race consists of six laps on the scenic Noland Trail, with short course sections before a..

The Harvest Hustle 10k and 5k is a trail running event held at Walnut Creek Park near Charlottesville. The race features a challenging cross-country course with elevation changes, rocks, and roots, offering a scenic and adventurous experience for participants. Runners receive a finisher’s medal, a t..

The Lake Anna Turkey Trot Half is a scenic and challenging race held at Lake Anna State Park, featuring a half marathon, 10k, and 5k courses. The half marathon is an out-and-back trail race with a 3-hour and 15-minute time limit, while the 10k and 5k courses combine trail and paved roads. Participan..

The Freight Train 100k/50k is a winter ultramarathon held in Farmville, Virginia, featuring race options of 100 kilometers, 50 kilometers, a half marathon, and a half marathon hike. The course follows a relatively flat rail trail with less than 1,500 feet of elevation gain for the 100k, making it a..

The Freight Train Ultra Marathon is held at High Bridge Trail State Park in Farmville, Virginia. It offers three distances: a half marathon, 50k, and 100k, all on a flat rail trail with under 1000 feet of elevation gain. The course features scenic stretches including the iconic High Bridge, with aid..