Trail Running calendar near Winchester 2025-2026

The Dark Side 8 Hour Ultra is an annual trail running event held at Little Bennett Park in Clarksburg, MD. Participants can run a 5.5-mile loop on scenic single-track trails for a total of eight hours, making it suitable for both competitive runners and those looking to enjoy the outdoors. The event..

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 part of a series of trail running races in Northern Virginia, featuring 5 and 10-mile courses. Set in a scenic location near the Capital Beltway, the event offers a mix of single-track and double-track trails, along with stream crossings, makin..

The Bigfoot Endurance 5 & 10 Mile Trail Race takes place at Rockburn Branch Park in Elkridge, Maryland. Participants can choose between a 5-mile run, a 10-mile run, or a 2-person relay for the 10-mile distance. The terrain is designed to be easy to moderate, making it suitable for both novice and ex..

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..

The Perfect Day 50K is an exciting endurance running event held at Massanutten's Western Slopes, where participants run a 5K every hour for 10 hours. This unique challenge allows individuals and teams to compete, with options for alternating loops or completing consecutive hours. The course features..

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 Spring Backyard Burn Trail Run at Laurel Hill is set to take place on March 16, 2025, in Lorton, Virginia. This event features two race options: a 5-mile and a 10-mile course, both of which traverse a scenic mix of forested and open meadow singletrack across 1,600 acres of former prison grounds...

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 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 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..

The Spring Backyard Burn Trail Run at Lake Fairfax Park in Reston, VA, offers participants a choice between a 5-mile and a 10-mile race. Set against the backdrop of a scenic lake and a well-maintained trail network, the course features smooth singletrack with some technical sections, providing a mix..

The Wild Trail 10K in Thurmont, MD, is a beginner-friendly trail race set in the scenic Thorpewood property. Scheduled for April 6, 2025, this event features both a 5K and a 10K race, both part of the FSRC Grand Prix series. Participants can enjoy a relaxed atmosphere, with no special gear required—..

The Chopawamsic Challenge is an exciting 50K and 100K trail race held in Prince William Forest Park. This event offers participants a chance to test their endurance on scenic trails, with over 90% of the course consisting of single track paths. Runners will experience significant elevation changes,..