Trail Running calendar near Woodstock 2026-2027

Experience one of the oldest 50 mile trail races in the country through the forested rolling terrain of Virginia. This spring event features a historic course through bluebells with a generous 13 hour time limit.

Run a scenic 5k cross-country course at a Virginia vineyard. The event welcomes runners and walkers alike and offers virtual participation options. It takes place in Warrenton on April 4, 2026.

Experience a hilly and technical trail race through the scenic property in Bluemont Virginia. Choose between the 5k and 10k distances and enjoy a glass of beer after conquering the technical terrain.

Experience a unique trail run on the private ThorpeWood estate in Maryland. Offering 5K and 10K distances, this club event features marked loops through beautiful natural terrain for FSRC members.

UltraTrax Wisp brings a timed trail adventure to Wisp Resort on April 11, 2026. Choose from four loop-based distances up to 28 miles, with stunning Appalachian views and a festive after-party. Finishers earn rewards, and part of the proceed..

Experience a scenic trail run at Pohick Bay Regional Park featuring waterfront views and historic surroundings. Choose between 5.9 and 10.4 mile courses through single track trails with professional support and activities for the whole fami..

Experience a fast and flat race along the scenic Chesapeake and Ohio Canal Towpath in Potomac. With 5k, 10k, and half marathon distances available, walkers and runners are invited to set new personal records at Carderock Park.

Join the Sip & Stride 5k and 10k in Louisa Virginia for a chance to earn points in the Sippin’ Series. Choose between in person racing or multiple virtual participation options with medals and shirts.

Choose from three scenic vineyard runs at Delfosse Winery. Tackle challenging summits for rewarding views across the 3k, 6k, or 9k courses. Virtual participation options are also available.

Rise Thermopylae is an immersive endurance challenge set in Virginia's wilderness. Choose from 6, 12, or 24 hour events that combine rucking, obstacles, and psychological tests. It's led by elite coaches and focuses on personal development..

Run Fest at Panorama Farms offers a day of trail racing and community celebration on April 18, 2026. Choose from a 4-mile trail race, a team relay, or a 1-mile fun run, followed by a festival with live music and local food. It's a chance to..

Experience the scenic grounds of Barrel Oak Winery in Delaplane, Virginia, through 3k and 6k race options. This inclusive event welcomes both walkers and leashed pets for a day of activity in a beautiful vineyard setting.

Experience a trail run through Lake Fairfax Park in Reston featuring scenic lake views and smooth singletrack paths. Choose between 5.3 and 10.3 mile distances on a course with frequent short hills and minimal pavement.

A 100 mile ultramarathon on the historic C&O Canal towpath beside the Potomac River and Appalachian mountains. The course is one 40 mile loop plus two 30 mile loops with aid stations every 3 to 6.9 miles.

Experience the scenic trails of Third Winchester Battlefield Park with 5k, 10k, and half marathon distances. This historic Virginia event welcomes both runners and walkers for a beautiful spring race.

Experience a unique trail race through an active rock quarry at the Luck Stone Leesburg Plant. This 5K event supports environmental preservation and features family activities and awards for all ages.

An annual 5K at Marymount University on April 25, 2026, run on the Bluemont and Custis Trails with a post-race gathering, a virtual option, chip timing, and guaranteed shirts for early registrants.

Run a scenic 5k around the Bluemont Station Brewery property in Virginia. The event welcomes both runners and walkers and offers in-person and virtual participation options.

Experience the fourth annual trail run at Mount Aetna Adventist School in Hagerstown. Choose between a 3k or 5k course to support student projects and enjoy fitness within a community setting.

A multi-distance trail event at Agricultural History Farm Park featuring a 5-mile loop used for timed 3-, 6-, and 10-hour challenges plus a traditional marathon and 25K, with rolling hills and a well-stocked aid station.