Trail Running calendar near Annandale 2025-2026

The Farm Park Challenge is an exciting running event taking place at the Agricultural History Farm Park in Derwood, Maryland. Participants can choose from various challenges, including a marathon, 25K, and timed events of 3, 6, or 10 hours, all featuring a 5-mile loop course. The trail offers a mix ..

The Four Leaf Clover Project's Run for Prosperity is a scenic 5k event taking place at Bluemont Station Brewery & Winery. Participants can enjoy a chip-timed race, with awards for top finishers in various categories. The event also includes a virtual race option for those unable to attend in person...

The Massanutten Mountain Trails 100 Mile Run is a challenging ultra-marathon set in the scenic Massanutten Mountains of Virginia's Shenandoah Valley. This event features a rugged course with over 18,000 feet of elevation gain, demanding both physical endurance and mental resilience from participants..

The Fountainhead Half Marathon and 10K Trail Run, held in Fairfax Station, VA, offers challenging and scenic courses through Fountainhead Regional Park. Participants can choose between a half marathon (approximately 13.5 miles) and a 10K (approximately 6.9 miles), both featuring rugged terrain with ..

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 every hour, continuing until only one runner remains. Participants are supported by experienced staff and professional c..

The Happy Tail Wine Trail 5k is a fun and engaging running event taking place at 53rd Winery in Louisa, Virginia, on May 24, 2025. Participants can choose from a 5k run, a 1-mile fun run for children aged 5-13, or a 1-mile Dog Jog, allowing them to bring their furry friends along. The event supports..

The Barrel Oak 6k is a challenging running event set in the scenic Barrel Oak Winery, taking place on May 31, 2025. Participants can enjoy a cross-country route that includes gravel roads and hills, with the 6k consisting of two laps of the 3k course. The event welcomes walkers and leashed pets, and..

The More Miles Last One Standing Challenge is an annual running event featuring a unique "last one standing" format. Participants race on a 4.167-mile course, completing laps on the hour for as long as they can. The event culminates when only one runner remains capable of finishing within the time l..

The One Family Brewing 5k is a scenic running event taking place on June 7, 2025, 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 receiv..

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, and single-track trails. Established in 1979, this event emphasizes tradition and community, being entirely volu..

The Crooked Run Valley 10k is a scenic running event taking place on June 8, 2025, at Sky Meadows in Delaplane, VA. Participants can enjoy a challenging course that includes roots, rocks, and gravel hills, as the 10k consists of two laps of the 5k route. Runners receive a finisher's medal, a technic..

The OSS/CIA 50 Mile Night Run is a unique endurance event taking place in Prince William Forest Park, Virginia, on June 14, 2025. Participants will tackle a challenging 50-mile course that consists of a 25+ mile loop run primarily on single track trails, with some fire road sections. The event pays ..

The Juneteenth Menare Foundation 12k and 6k event is a trail running race celebrating Juneteenth, taking place at Button Farm through the scenic Schaeffer Farm Trails. Participants can enjoy a challenging course, with walkers also welcome. Runners will receive a finisher’s medal, a technical event s..

The Blue Crab Bolt Trail Run at Seneca Creek State Park in Gaithersburg, MD, is an exciting event that marks the beginning of the 14th Blue Crab Bolt Trail Running Series. Participants can choose between a 5K (approximately 3.3 miles) and a 10K (approximately 6.4 miles) course, both featuring scenic..

The Cacapon 12 Hour Challenge is an exciting endurance running event set in Berkeley Springs, WV, featuring a scenic and challenging five-mile loop trail. Participants will navigate a moderately to very technical course with approximately 750 feet of elevation change per loop. The event includes wel..

The Sweet Air Trail Race, organized by the Baltimore Road Runners Club, is a 7-mile running event set to take place at Gunpowder State Park. This exciting race features a challenging course that includes rolling hills, fast sections, and water crossings, with participants crossing from Harford Count..

The Winery 10k is part of the 53rd Winery 5k & 10k event, taking place on July 13, 2025, at the scenic 53rd Winery in Louisa, Virginia. This race welcomes both runners and walkers, offering a virtual option for those unable to attend in person. Participants will receive a glass of wine, a finisher's..

Leopold's Preserve 10k is a trail running event taking place on July 13, 2025, at Leopold's Preserve in Broad Run, Virginia. Participants can enjoy a scenic course that features a mix of dirt paths and natural terrain. The event is open to walkers and includes a virtual race option for those unable ..

The 868 Estate Vineyards 10k is a scenic running event taking place on July 26, 2025, at the picturesque 868 Estate Vineyards. Participants can enjoy a challenging cross-country course featuring hills, with the 10k consisting of two laps of the 5k route. Runners will receive a glass of wine, a finis..

The Blue Crab Bolt at Schaeffer Farms is an exciting trail running event featuring 5K and 10K courses that showcase the beautiful and well-maintained trails of Schaeffer Farms in Germantown, MD. Participants can expect a mix of fast, flowy paths, technical sections, and scenic views, starting and en..