Trail Running calendar near Chesterfield 2025-2026

The Sip & Stride 10k is a running event taking place at Southern Revere Cellars, featuring both 5k and 10k distances. Participants can enjoy a scenic cross-country course, with the 10k consisting of four laps around the winery property. Runners receive a technical event shirt, a glass of wine or bee..

The Women's Trail Festival, taking place on March 29-30, 2025, in Williamsburg, VA, is a vibrant running and hiking event designed to celebrate women in sports. Participants can choose between a competitive 10-mile trail race and an 8k trail run, as well as non-competitive hiking options. The course..

The Appomattox River Regional Park 5K Trail Run is an exciting running event scheduled for March 29, 2025, in North Prince George, Virginia. Participants can choose to run or walk the 5K course, with all entrants receiving a medal. Awards will be given to the top three overall male and female finish..

The Mountain & Vine Vineyard 9k is a scenic running event taking place at the picturesque Mountain & Vine Vineyards. Participants can choose from three distances: 3k, 6k, and 9k, with the 9k course featuring challenging hills and stunning views. Runners will receive a glass of cider, a finisher meda..

The 1781 Brewery 10k is a scenic cross-country trail run taking place at the historic 1781 Brewing Company, located on the Chancellorsville and Wilderness battlefields. Participants can enjoy a challenging course with hills, and both runners and walkers are welcome. Each participant receives a finis..

The Sheetz-to-Sheetz Trail Run is a unique 14-mile untimed race held in King George, Virginia, designed to benefit local charities. Participants start at one Sheetz convenience store and finish at another, traversing the scenic Dahlgren Railroad Heritage Trail. The event emphasizes enjoyment over co..

The Wisdom Oak Winery 10k is a scenic running event held at the picturesque Wisdom Oak Winery, featuring a challenging cross-country course that includes rolling hills and gravel roads. Participants can enjoy a glass of wine post-race, along with a finisher's medal and a technical event shirt. The e..

The James River Trail Runs is an exciting ultra-running event taking place at James River State Park, featuring multiple distance options including a 10 miler, 50K, and 50 mile relay and solo races. The course consists of a challenging 10-mile loop with significant elevation changes and scenic views..

The Virginia Run for Cancer is a unique running event scheduled for April 26, 2025, in Hampton, VA. Participants can choose to compete individually or as part of a team in a 24-hour race format. The event aims to raise funds for the American Cancer Society, with a lifetime total of $310,000 raised t..

The Dominion Energy Riverrock Trail Running Events, taking place from May 16 to May 18, 2025, in Richmond, VA, features a variety of races including the Belle Isle Blitz (5k), James River Scramble (10k), and Bust the Banks Half Marathon. This outdoor sports festival, organized by Sports Backers and..

The Happy Tail Wine Trail 5k is a fun and engaging running event held at 53rd Winery in Louisa, Virginia. Participants can choose from a 5k run, a 1-mile fun run for children ages 5-13, or a 1-mile Dog Jog, allowing them to bring their furry friends along. The event supports the Louisa Humane Societ..

The Taskinas Creek Half Marathon, taking place at York River State Park in Williamsburg, VA, offers a unique running experience on June 1, 2025. This event features a challenging course that includes a mix of single track trails, fire roads, and a short road section, with scenic views and rolling te..

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 exciting running event taking place at High Bridge Trail State Park in Farmville, VA. Celebrating its 7th year, the event features three distances: a 50K, a Half Marathon, and a sunset 5K. Runners will traverse a scenic rail trail rich in Civil War history..

The High Bridge Challenge is an exciting running event taking place on the scenic High Bridge Trail State Park in Virginia. Participants can choose from various race combinations, including distances of 26K, Marathon, 100K, and 150K, by completing both the Night Train and Freight Train races. The Ni..

The Night Owl 9K is an exciting running event taking place at Freedom Park in Williamsburg, VA. This challenging race features a mix of single track, fire road, and paved trails, with rolling hills and technical sections. Participants can enjoy a post-race party with beer and pizza, and all finisher..

The Winery 10k is part of the 53rd Winery's annual running event, which also includes a 5k race. This event takes place at the scenic 53rd Winery in Louisa, Virginia, and features a cross-country course around the vineyards. Participants can enjoy a chip-timed race, receive a finisher's medal, a tec..

The Dahlgren Heritage Rail Trail 50K is a challenging trail race set to take place in King George, Virginia, on August 2, 2025. Participants will navigate a flat, well-maintained course primarily composed of dirt, grass, and gravel, providing a scenic and shaded running experience. The race features..

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, scheduled for August 2, 2025, in King George, VA, offers participants a scenic out-and-back course along the Dahlgren Railroad Heritage Trail. This flat and smooth trail, ideal for running, features a variety of surfaces and is shaded by trees, providing a comfortable env..