Trail Running calendar near Winchester 2025-2026

The Ed Poling Memorial Hike for Hunger & Hope is a non-competitive fundraising event suitable for all ages, featuring hikes of varying distances along the scenic C&O Canal towpath in Maryland. Participants can choose from a 4K, 10K, or half marathon hike, catering to both casual and serious hikers...

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 More Miles Last One Standing Challenge is an endurance running event held in Knoxville, Maryland, featuring a unique "last one standing" format. Participants run a 4.167-mile loop, known as "the yard," every hour on the hour, continuing as long as they can complete the loop within the hour. The..

The Dash Through the Dirt Half is a scenic running event held at Carderock Recreation Area along the Chesapeake & Ohio Canal Towpath in Potomac, Maryland. Featuring a half marathon, 10k, and 5k, the courses are fast, flat, and run on a light gravel dirt trail, ideal for personal records. Each route..

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 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 Half Ass 25k & 10k is a challenging trail running event held in Newville, Pennsylvania, at 1599 Doubling Gap Road. The race offers two distances: a 10k with over 2,000 feet of elevation gain, and a more demanding 25k featuring over 4,000 feet of vertical gain, including iconic park highlights li..

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 Highlands Sky 40 Mile Trail Run is a premier ultramarathon held annually in Davis, West Virginia, primarily within the Monongahela National Forest. Starting and finishing at Canaan Valley State Park, the challenging 40-mile course traverses rugged and scenic terrain including the Roaring Plains..

The OSS/CIA 50 Mile Night Run is a challenging ultramarathon held in Prince William Forest Park, Triangle, Virginia, a historic site once used to train OSS spies during World War II. The event features a 50-mile race consisting of two laps on a 25+ mile loop primarily on single-track trails, fire ro..

The Juneteenth Menare Foundation 12k and 6k is a trail running event held at Button Farm in Germantown, Maryland, celebrating Juneteenth. The race features a challenging, hilly, and scenic course that loops through the Schaeffer Farm Trails, with the 6k consisting of one lap and the 12k two laps. Wa..

The Canaan Valley Trail Run, scheduled for June 21, 2025, in Canaan Valley State Park, offers an exciting opportunity for runners of all levels. Participants can choose between a 5.9-mile single loop or an 11.8-mile double loop on the scenic Promised Land Trail. Each runner will receive a finisher m..

The Blue Crab Bolt Trail Run at Seneca Creek State Park in Gaithersburg, MD, is a scenic trail running event featuring 5K (3.3 miles) and 10K (6.4 miles) distances with elevation gains of 200 and 450 feet, respectively. Set amidst lake views, streams, and miles of singletrack trails, the course offe..

The Catoctin 50k Trail Run & Half Cat is a challenging ultramarathon held in Frederick, Maryland, within Cunningham Falls and Gambrill State Parks. The 50k course is an out-and-back route on rocky, demanding trails marked by light blue blazes, featuring significant elevation changes and multiple str..

The Cacapon 12 Hour Challenge is a trail running event held in Berkeley Springs, West Virginia, featuring a scenic, moderately to very technical five-mile single-track loop. The course includes about 750 feet of elevation change per loop, with some stream and road crossings on lightly-traveled park..

The Leopold’s Preserve 10k is a trail running event held at Leopold’s Preserve in Broad Run, Virginia. Participants can enjoy a mostly flat dirt course with some roots, featuring scenic views of a diverse habitat and wildlife. The race is chip-timed and includes a finisher’s medal and technical even..

The 868 Estate Vineyards 10k and 5k is a scenic cross-country race held at 868 Estate Vineyards. Participants can choose between a 5k or 10k course around the vineyard property, featuring hills and beautiful views. The event includes a finisher medal, technical event shirt, and a glass of wine.Point..

The Blue Crab Bolt Trail Run at Schaeffer Farms in Germantown, MD, is a trail running event featuring 5K and 10K++ distances (about 6.7 miles). The course offers a flowy, fast, and fun experience on well-maintained trails with twisty single-track sections, stream crossings, log ramps, some hills, an..

The Blue Crab Bolt Trail Run at Little Bennett is a scenic trail running event held in Little Bennett Regional Park, Montgomery County, Maryland, about 30 miles west of Washington, D.C. The park offers a 3600-acre wooded area with over 20 miles of trails, streams, and camping facilities. The race fe..

The Third Winchester Battlefield Half, held on August 9, offers scenic trail routes through the historic battlefield. Participants can choose from a half marathon, 10k, or 5k race, with the half marathon consisting of three loops on a light gravel dirt path. The event features chip-timed results, fi..