Trail Running Calendar Virginia 2025-2026

The Night Raider 10k and 5k is a scenic trail run held at the Manassas National Battlefield, starting and ending at The Winery at Bull Run in Centreville, VA. Participants can enjoy a course that includes cross-country paths, dirt trails, a boardwalk, and gravel sections, with some hills. The event..

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 virtual running event benefiting the Louisa Humane Society in Louisa, Virginia. Traditionally held at 53rd Winery, the course features a scenic, mostly flat cross-country route around vineyards and winery grounds. The event includes a 5k run, a 1-mile fun run for ch..

The Capital Backyard Ultra is an endurance running event held in Lorton, Virginia, featuring a unique format where participants run a 4.167-mile loop every hour until only one runner remains. The race supports experienced backyard ultrarunners aiming to push their limits, with a maximum of 60 partic..

The Barrel Oak 6k is a challenging cross-country running event held at Barrel Oak Winery in Delaplane, VA. Participants can choose between a 3k or 6k race, with the 6k being two laps of the 3k course. The event features scenic routes through vineyards, gravel roads, and hills.Runners receive a finis..

The Taskinas Creek Half Marathon is a mostly trail-based race held at York River State Park in Williamsburg, Virginia. The course features a mix of single track mountain bike trails, fire road trails, and about one mile of pavement, with rolling terrain and approximately 600 feet of elevation gain...

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 One Family Brewing 5k is a scenic cross-country race held at One Family Brewing in Lovettsville, Virginia. The 5k course consists of three laps around the brewery's perimeter fields, offering a fairly flat but natural terrain. Participants receive a glass of beer, a finisher’s medal, a technical..

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 Old Dominion 100 Mile Endurance Run is a challenging ultramarathon held in Fort Valley, Virginia, featuring a measured loop course through the Massanutten Mountains and Shenandoah River Valley. The race covers 100 miles with 14 significant climbs totaling 14,000 feet of elevation gain. Participa..

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 Crooked Run Valley 10k, held at Sky Meadows in Delaplane, Virginia, is a challenging trail race featuring a scenic 5k loop with roots, rocks, and a gravel hill, with the 10k consisting of two laps of this course. The event welcomes runners and walkers, offering chip timing, finisher medals, and..

The OSS/CIA 50 Mile Night Run is a challenging ultramarathon held in Prince William Forest Park, Virginia, known for its historical ties to the U.S. intelligence community. The race features a 50-mile course primarily on single-track trails, with some fire roads and crossings, run twice to complete..

The Night Train 50K and Half Marathon is an annual nighttime trail running event held at High Bridge Trail State Park in Farmville, Virginia. The race features three distances: a 50K, a half marathon, and a sunset 5K, all following a historic rail trail through scenic countryside and small towns. Th..

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 High Bridge Challenge is a multi-distance trail running event held at High Bridge Trail State Park in Virginia. Participants can choose from various race options, including 26K, marathon, 100K, and 150K, with the opportunity to complete combined "train" races in June and December for special awa..

The Last Stand Army Backyard Ultra is a challenging endurance race held in Midlothian, Virginia, on Flag Day, June 14, 2025, to honor the 250th Birthday of the U.S. Army. Participants run a 4.167-mile loop every hour on the hour, continuing until only one runner remains to complete a final loop.The..

The Froggy Mountain 100 is an ultramarathon held in Galax, Virginia, featuring 50- and 100-mile race options on a challenging 1-mile loop course with approximately 500 feet of vertical gain per loop. Known as one of the toughest courses in the country, the event takes place entirely on private prope..

The Night Owl 9K is a challenging trail race held at Freedom Park in Williamsburg, Virginia. The 9-kilometer course features a mix of single track, fire road, and paved trails with rolling hills and technical sections including roots and twists, offering a mountain bike trail-like experience. The ra..

The Hybrid 8K is a unique running event held in Danville, Virginia, that combines both trail and road running for an exciting race experience. Participants start at Anglers Park, running 2.5 miles on the Withcback trail through the woods, followed by a 2.5-mile finish on the road and the rolling Riv..