Trail Running calendar near Chesterfield 2025-2026

The Freight Train Ultra Marathon is held at High Bridge Trail State Park in Farmville, Virginia, offering distances of a half marathon, 50k, and 100k. The course is a flat rail trail with minimal elevation gain, featuring scenic views including crossing the historic High Bridge twice. The 100k route..

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 Tinsel Trot 10k in Louisa, VA, is a festive cross-country running event held at Southern Revere Cellars. The course loops around the winery property, with the 10k consisting of four laps and the 5k two laps, featuring gentle terrain without major hills. Participants enjoy a chip-timed race with..

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..

The Willis River event in Cumberland, VA, offers runners three distance options: 50K, 35K, and 20K. The 35K course follows much of the Willis River Trail, featuring stream crossings, rolling hills, and guaranteed wet feet. The 50K combines the 35K route with an additional 10-mile Bear Creek segment,..

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 ICY-8 Spotsylvania Courthouse is an annual trail running event held at Lake Anna State Park in Spotsylvania, Virginia. Featuring an 8-hour adventure trail run and a concurrent half marathon+, the race offers a unique figure-8 course composed of three loops: an 8.0-mile long loop, a 4.7-mile shor..

The Holiday Lake 50K, held in Appomattox, Virginia, is a well-established ultra trail race founded in 1996. It features a scenic loop course around Holiday Lake, combining country roads and trails, making it ideal for first-time ultra runners as well as seasoned athletes. The event also includes 10K..

The RRRC Bear Creek 10 Mile Trail Run will take place in Cumberland on Sunday 22 February 2026. You can run 10 miles.

The Dogwood Ultra Marathons, held at Twin Lakes State Park in Green Bay, Virginia, is a challenging multi-day event featuring a 3.42-mile rolling loop course with about 400 feet of elevation change and stream crossings. The race offers various distances and formats, including 10-mile runs, 12-hour a..

The Women's Trail Festival, held in Williamsburg, VA at Freedom Park, is a two-day event featuring both competitive and noncompetitive trail running and hiking options. Participants can choose between a challenging 10-mile loop course with 700 feet of elevation gain, including single track mountain..

The Sheetz-to-Sheetz Trail Run is a 14-mile untimed point-to-point trail run held in King George, Virginia. Starting at a Sheetz convenience store near King George Middle School, the course follows rural roads briefly before transitioning to the flat, well-marked Dahlgren Railroad Heritage Trail, a..

The James River Trail Runs, held at James River State Park in Gladstone, Virginia, offer a variety of trail running distances including a 10 miler, 50K, 50 mile relay, and 50 mile solo race. The course consists of a challenging 10-mile loop featuring 1,025 feet of climbing, with the first half invol..

The Sip & Stride 10k is a cross-country running event held at Southern Revere Cellars in Louisa, Virginia. The course loops around the winery property, featuring a mostly flat terrain with no major hills. Participants in the 10k complete four laps, while the 5k involves two laps.Runners receive a te..

The Mountain & Vine Vineyard 9k is a scenic and challenging race held at Mountain & Vine Vineyards in Faber, Virginia. The event offers three distances: 3k, 6k, and 9k, with the 9k consisting of three laps around a hilly course featuring some tough summits and rewarding views. Participants receive a..

The Virginia Run for Cancer is a 24-hour solo and team ultramarathon held in Hampton, Virginia, featuring a USATF-certified 3.75-mile all-dirt nature park trail. The event welcomes runners and walkers of all abilities, offering a flat course ideal for endurance running. Participants can compete indi..