Trail Running calendar near Chesterfield 2025-2026

The Saint Marys Lake Trail Series is an exciting running event taking place in Leonardtown, MD, featuring three race distances: 50K, 34K, and 17K. Set against the scenic backdrop of Saint Mary’s Lake and the surrounding Salem Forest, participants will navigate a roughly 10.5-mile loop that combines..

The RRRC Bear Creek 10 Mile Trail Run is an exciting trail race organized by the Richmond Road Runners Club, taking place at Bear Creek Lake State Park in Cumberland, Virginia. The event features a challenging 10-mile loop course that traverses the scenic piedmont hills and includes a mix of single-..

The Running Ravens 5k is a fundraising event scheduled from March 7 to March 10, 2025, in Chester, Virginia. Participants can choose to run the 5k in person or opt for a virtual race. The course will traverse a cross-country trail, which is not suitable for strollers, dogs, or wheelchairs. Registrat..

The Naked Creek Trail Race, scheduled for March 8, 2025, in Earlysville, VA, features two main events: a 25K and a 10K race. Both courses are predominantly wooded, offering approximately 90% single and double track trails, with stunning views of the South Fork Rivanna River Reservoir and the Blue Ri..

The Last Stand Loch Lothian Backyard Ultra is an exciting endurance event set to take place in Midlothian, Virginia. This unique race challenges participants to complete a 4.18-mile loop within one hour, with the goal of being the last runner standing. The event is designed for both seasoned ultra-r..

The Dogwood Ultra Marathons, celebrating its 10th year, offers a variety of endurance events at Twin Lakes State Park in Virginia. Participants can choose from 10-mile, 12-hour, 24-hour, and 48-hour races, including solo and relay options. The course features a 3.35-mile loop with elevation changes..

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 is a two-day running and hiking event taking place at Freedom Park in Williamsburg, VA. Scheduled for March 29-30, 2025, the festival features a competitive 10-mile trail race and an 8k trail hike, along with non-competitive options for both distances. Participants can enj..

The Appomattox River Regional Park 5K Trail Run is an exciting running event taking place in N. Prince George, Virginia. Scheduled for March 29, 2025, participants can choose to run or walk the scenic 5K trail.Registration fees vary, with discounts available for students and couples. All participant..

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 Sheetz-to-Sheetz Trail Run is a unique 14-mile point-to-point running event held in King George, Virginia. This untimed race starts at one Sheetz convenience store and ends at another, traversing scenic farmland and forest along the Dahlgren Railroad Heritage Trail. Participants can enjoy a rela..

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 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 solo or as part of a team in a 24-hour race, with awards for top finishers and special recognition for fundraising efforts. The course is a flat, certified 3.75-mile..

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, set in York River State Park, Williamsburg, VA, offers a unique trail running experience. Scheduled for June 1, 2025, this event features a challenging course that includes single track trails, fire roads, and a short road section, with a total elevation gain of aro..

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..