Trail Running calendar near Chesterfield 2025-2026

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 Terrible Twelve is a 12-hour endurance running event held at the Warhill Nature Trail in Williamsburg, Virginia. Participants run or walk as many 3.7-mile loops as possible from 7 PM to 7 AM on a crushed gravel trail featuring rolling hills. Unique to this race, each runner must volunteer for on..

The Orchard Dash 10k is a cross-country trail running event held at Albemarle CiderWorks in North Garden, Virginia. Featuring a challenging course with plenty of hills, the 10k consists of two laps of a looped trail, while a 5k option completes one lap. Participants enjoy a chip-timed race with wate..

The Roanoke Canal 5k is a trail running event held in Roanoke Rapids, North Carolina, following the historic Roanoke Canal Trail built in 1823. The course features a natural surface with mostly flat terrain and some hills, passing over original canal culverts and a large bulkhead once used for mill..

The Pawpaw 10 Miler and 5 Miler is an annual running event held at Powhatan State Park in Powhatan, Virginia. The race features a scenic 10-mile course along the James River, through open fields, shaded singletrack trails, and past historic cabin ruins, offering a mix of flat, fast riverfront terrai..

The Run the Vineyards - Wind Vineyards 5K is a scenic race held at Wind Vineyards in Tappahannock, Virginia, featuring a 5K course on well-maintained trails of hard-packed dirt and grass across a 200-acre property. The mostly flat course includes two short hills and is chip-timed with awards for top..

The Run to the Taproom - Creekside Farm Brewery 5K & 8K is a scenic running event held at Creekside Farm Brewery in King George, Virginia. Participants can choose between a 5K or 8K race along well-maintained, non-technical dirt trails that wind through a 1,000-acre farm bordering the Rappahannock R..

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 varied terrain for runners. Participants also have the option to run a 1-mile distan..

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 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, offering scenic fall foliage and birdwatching opportunit..

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, with the 10k consisting of two laps of the 5k out-and-back route. Participants enjoy a vibrant atmosp..

The Bivanna Trail Extravaganza will take place in Charlottesville on Saturday 18 October 2025. You can run between 10 and 40 miles.

The Heart of Virginia Council Glow Trail Run 5K is a unique nighttime trail running event held at Camp Brady Saunders in Maidens, Virginia. This family-friendly race welcomes participants of all ages and is open to everyone, not just Scouts. The course features a 5K trail illuminated with glow-in-th..

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

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 event features a USATF-certified 2.215-mile loop course on a mainly flat, scenic, crushed gravel trail with minimal elevation cha..

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 the solo 50K or join a relay team of 2 to 6 members, collectively completing six laps on the scenic Noland Trail, with short course sections before..

The Harvest Hustle 10k in North Garden, Virginia, is a cross-country trail run held at Walnut Creek Park near Charlottesville. Featuring a challenging course with elevation changes, rocks, and roots, the event offers both 5k and 10k distances. Runners enjoy a chip-timed race with finisher medals and..

The Lake Anna Turkey Trot Half is a scenic and challenging running event held at Lake Anna State Park in Spotsylvania, Virginia. It features three race distances: a 5k trail run, a 10k that is half trail and half paved road, and a half marathon with a similar mixed course. Walkers are welcome, and t..

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 Run for Valor 10K is a trail running event held at Valor Ranch in King George, Virginia. The race features a 10K run, a 10K weighted ruck, a 5K run, and a 1-mile fun run/walk suitable for all ages and paces. The course traverses farm trails, pastures, woods, and gravel roads, with uneven terrain..