Trail Running calendar near Woodstock 2025-2026

The Dark Side 8 Hour Ultra is an annual trail running event held at Little Bennett Park in Montgomery County, MD. Participants can run as many laps as they wish on a scenic 5.5-mile loop, primarily on single track trails. This timed event encourages runners to enjoy the outdoors as spring approaches..

The Paradise Springs 10k is a challenging trail running event held at Hemlock Overlook Park, featuring a scenic course with significant elevation changes and technical sections. Participants can enjoy a glass of wine from Paradise Springs Winery post-race, along with a finisher medal and a technical..

The Spring Backyard Burn Trail Run at Wakefield Park is a thrilling event scheduled for March 2, 2025, featuring both 5-mile and 10-mile trail races. Set in Annandale, Virginia, the course offers a mix of scenic single-track and double-track trails, along with shallow stream crossings, making it an..

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 MCRRC Seneca Creek Greenway Trail Marathon & 50K is a running event scheduled for March 8, 2025, in Gaithersburg, Maryland. Participants can choose between two challenging distances: a marathon and a 50K. This event is organized by the Montgomery County Road Runners Club (MCRRC) and aims to prov..

No Man's 50K is a unique trail running endurance challenge designed exclusively for women, with the support of family and friends. Established in 2016, the event aims to promote female participation in trail races. Participants can choose between two distances: 25K and 50K, with a generous 9-hour cu..

The Perfect Day 50K is a unique endurance running event held at Massanutten's Western Slopes, where participants run a 5K every hour for 10 hours. This event allows individuals and teams to compete, with options for teams of two or three to alternate loops. Each participant must complete the 5K loop..

The Bel Monte Endurance Races are held in the stunning George Washington National Forest in Virginia's Blue Ridge Mountains. This premier spring ultra event features three race distances: a 50-mile, a 50K, and a 25K, with courses that are predominantly single track trails and mountain roads. Partici..

The Spring Backyard Burn Trail Run at Laurel Hill is set to take place in Lorton, Virginia, featuring both 5-mile and 10-mile race options. The scenic course winds through 1,600 acres of former prison grounds, offering a mix of forested and open meadow singletrack trails. Participants will start and..

The Molon Lave 5k is a scenic running event held at Molon Lave Winery, featuring a cross-country course that welcomes both runners and walkers. Participants can choose to run in person or opt for a virtual race option. Each runner receives a finisher's medal, a technical event shirt, and a glass fro..

The Battle of Kelly's Ford is a cross-country running event taking place at the scenic Kelly's Ford Inn in Remington, Virginia. Participants can choose between two races: a 6Km race for women and girls, and an 8Km race for men and boys. The course features a 2Km loop that combines close-cut grass an..

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 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 Hone Quarry Ultra is a challenging 40-mile trail endurance race set in the picturesque Shenandoah Valley, starting and finishing at Briery Branch. Participants will navigate through the George Washington National Forest, experiencing stunning landscapes, including cliffs, meadows, and waterfalls..

The Smoketown Brewery 10k is a scenic running event taking place on March 30, 2025, near Smoketown Brewery in Brunswick, MD. Participants can enjoy a flat, light gravel dirt path while competing for points in the Year-Long 5k, 10k, and Sippin Series. The event welcomes walkers and offers a virtual r..

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 Bull Run Run 50 Miler is a challenging trail running event held in Clifton, Virginia, featuring a scenic 50-mile course that runs alongside the Occoquan River and the historic Bull Run. Scheduled for April 5, 2025, this race showcases the natural beauty of the area, particularly during spring wh..

The Massanutten King of the Mountain 18 Miler is an exciting running event set to take place in McGaheysville, Virginia. This challenging course features a mix of trails, gravel, and roads, offering participants scenic views and a rewarding experience. Runners will start at Massanutten Base Camp, na..

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 Breeze Thru the Trees 5k is a cross-country running event taking place at Ruppert Nurseries in Gaithersburg, Maryland, on April 6, 2025. Participants can choose between a 5K run and a 1-mile fun run, both set in a scenic tree nursery within Montgomery County’s Agricultural Reserve. Proceeds from..