Trail Running calendar near Williamsburg 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 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 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 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..

Haunts & Hallows is a half marathon trail race held in Virginia Beach, VA, at First Landing State Park. The course features gently rolling trails with about 300 feet of elevation gain, including roots, bridges, and sandy sections, offering scenic and varied terrain. The event fosters a supportive co..

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 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..

The Pocahontas Half is a scenic running event held at Pocahontas State Park near Richmond, Virginia. It features a half marathon, 10k, and 5k race, all taking place on the forested Bright Hope Trail, which offers a soft dirt and pine needle surface with some minor hills. The half marathon course is..

The Mel Williams Memorial Seashore 50K, presented by Brooks, is a challenging trail ultramarathon held at First Landing State Park in Virginia Beach, VA. The race features a two-loop course starting and finishing at the park's boat ramp, covering 50 kilometers (31 miles) through scenic trails. Runne..

The Snowy Owl 10 Mile is a challenging trail race held at York River State Park in Williamsburg, Virginia. The course features a mix of terrain including five miles of technical single track, dirt fire road trails, about three-quarters of a mile on paved road, rocky sections, twisting trails, and a..

Chills In The Mill: Harwoods Half Marathon & 5K is a winter running event held at Harwoods Mill Park in Yorktown, Virginia. The event features a half marathon and a 5K race, with a combined limit of 350 participants. The course includes a mix of wide trail roads and single-trail bicycle paths, marke..

The Dahlgren Trail Half Marathon will take place in King George on Saturday 31 January 2026. You can run 13 miles.

The Swammie Shuffle 200 is an ultramarathon held in Virginia Beach, VA, covering over 200 miles. Runners start at Sandbridge Beach and head south through the Outer Banks of North Carolina to the Cape Hatteras Lighthouse, then return to the start. The course features scenic beach stretches, sidewalks..