Trail Running Calendar Virginia 2025-2026

The Virginia Creeper 10 Miler is a running event taking place in Abingdon, Virginia, on May 24, 2025. This race features an out-and-back course along the scenic Virginia Creeper Trail, primarily consisting of dirt and gravel surfaces. Participants will run five miles out before turning around to com..

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 Capital Backyard Ultra is a unique endurance running event held in Lorton, Virginia, designed for a maximum of 60 participants. The race features a 4.167-mile loop that starts on the hour, with runners competing until only one remains. The event emphasizes camaraderie and support among experienc..

The Barrel Oak 6k is a challenging running event set in the scenic Barrel Oak Winery, featuring a cross-country route that includes gravel roads and hills. Participants can enjoy a fun atmosphere, with options for both runners and walkers, as well as leashed pets. The event supports the Semper Fi an..

The Conquer the Cove Marathon Trail Race, hosted by Mountain Junkies, is set to take place on June 1, 2025, at Sherwood Archers in Roanoke, Virginia. This event features both a 25k and a marathon distance, with a challenging course that includes significant elevation gain, particularly in the marath..

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 time limit of 4.5 hours. Re..

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 8th Annual Dam Yeti 55K/50 Mile Endurance Run is a premier trail running event taking place in the scenic Appalachian region. This point-to-point race features a USATF certified course along the Virginia Creeper Trail, offering breathtaking views and a smooth route. Participants can choose betwe..

The One Family Brewing 5k is a scenic running event taking place at One Family Brewing in Lovettsville, VA. Participants will complete three laps around the brewery's cross-country course, with a virtual race option available for those unable to attend in person. Runners will receive a finisher's me..

The Old Dominion 100 Mile Endurance Run is a challenging ultramarathon held annually in Virginia, featuring a diverse course that includes various terrains such as pavement, gravel roads, single track trails, and more. Established in 1979, this event emphasizes tradition and community, being entirel..

The Crooked Run Valley 10k is a scenic running event taking place in Sky Meadows, Delaplane, VA. Scheduled for June 8, participants can also opt for a 5k distance. The race features a challenging trail with roots and rocks, and runners will receive a finisher's medal, a technical event shirt, and ch..

The OSS/CIA 50 Mile Night Run is a unique endurance event set in the historic Prince William Forest Park, which served as a training ground for the OSS, the precursor to the CIA. Participants will tackle a challenging 50-mile course that consists of a 25+ mile loop run twice, primarily on single-tra..

The Night Train 50K and Half Marathon is an exciting running event taking place on June 14, 2025, at High Bridge Trail State Park in Farmville, VA. Participants can choose from three distances: a 50K, a half marathon, and a sunset 5K. The course features a scenic route along an old rail trail, showc..

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 Jackson River Scenic Trail Marathon, Half Marathon, 10k, and 5k is a vibrant running event taking place in Covington, Virginia. The USATF certified course starts and ends at the Intervale Trail Head, following a scenic route along the Jackson River. Participants can enjoy a smooth, mostly flat t..

The Froggy Mountain 100 is an exciting running event taking place in Galax, VA, featuring both 50 and 100-mile races on a challenging one-mile loop course with approximately 500 feet of vertical gain per loop. Participants can enjoy aid stations with hot food available throughout the event, which ha..

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..

Leopold's Preserve 10k is a trail running event taking place at Leopold's Preserve in Haymarket, Virginia. Participants can enjoy a scenic course that features a mix of dirt paths and natural terrain. The event is part of a series where points are accumulated towards year-long competitions.Runners r..

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 868 Estate Vineyards 10k is a scenic running event taking place at the picturesque 868 Estate Vineyards. Participants can choose between a 5k and 10k distance, with both races contributing points towards various year-long series. Runners will receive a glass of wine, a finisher medal, a technica..