Trail Running calendar near Winchester 2025-2026

The Blue Crab Bolt Trail Run at Seneca Creek State Park in Gaithersburg, MD, is the opening race of the 15th annual Blue Crab Bolt Trail Running Series. Scheduled for June 21, 2025, it offers 5K (3.3 miles) and 10K (6.4 miles) trail races featuring scenic singletrack trails, lake views, and streams..

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 Canaan Valley Trail Run is an annual trail running event held in Canaan Valley State Park, Davis, West Virginia. Scheduled for June 21, 2025, it offers two race distances: a 5.9-mile single loop and an 11.8-mile double loop on the scenic Promised Land Trail, which starts and finishes behind the..

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, a 380-acre nature conservancy in Haymarket, Virginia. The course features mostly flat, dirt paths with some roots, offering a scenic and natural running experience. The 10k route is an out-and-back course with a detour o..

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, offers a fun and moderately technical trail running experience on well-maintained, flowy trails. The course features twisty single-track paths, stream crossings, log ramps, some hills, rocky and rooty sections, and open farm field ru..

The Lost Turkey Trail Races, held in Imler, Pennsylvania, offer challenging trail running events through Central Pennsylvania’s scenic ridges and valleys. The race features a grueling 50k point-to-point course along the Allegheny Front, culminating at Blue Knob, as well as a half-marathon loop and a..

The Blue Crab Bolt Trail Run at Little Bennett is a scenic trail running event held at Little Bennett Regional Park in Clarksburg, 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 feature..

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..

The MD Heat Trail Race, held in Elkridge, Maryland at the Patapsco Pickall Area, offers challenging trail running distances of 25K and 50K. The course features rolling single-track trails with over 2,000 feet of elevation gain, including technical rocky sections, two river crossings, and a short pav..

The Miner's Lady 8-Hour is an endurance running event held in Harpers Ferry, West Virginia, where the Blue Ridge Mountains meet the Shenandoah River. Participants run a challenging 10K loop featuring 850 feet of elevation gain, primarily on single-track trails that pass waterfalls and creek crossing..

The Inferno 10k is a challenging trail running event held at Dirt Farm Brewing in Bluemont, Virginia. The course features rugged forest terrain with steep inclines, descents, and technical sections including tree roots and rocks. The 10k race consists of two loops of a winding trail behind the brewe..

The Vineyard Vista 10k and 5k is a scenic running event held at Muse Vineyards in Woodstock, VA. Participants can enjoy a course that combines cross-country around vineyards, paved road sections, and trail segments through Seven Bends State Park. The event benefits Friends of Seven Bends State Park..

Trails 4 Tails in Hanover, PA, is a trail running event held at scenic Codorus State Park, featuring a 5.72-mile loop course around Lake Marburg with single track trails and shoreline views. The event offers three race distances: a 40-mile ultra consisting of seven loops with approximately 4,200 fee..

The VHTRC Women's Half Marathon will take place in Fairfax Station on Saturday 13 September 2025. You can run between 7 and 13 miles.

The 12 Hour Adventure Trail Run takes place at Prince William Forest Park near Triangle, Virginia. This challenging event features a 6.5-mile figure-eight loop trail course with approximately 650 feet of elevation gain per loop, combining single track and fire road terrain. The course is designed to..

The Rock 'N The Knob Trail Challenge, held in Claysburg, Pennsylvania, is the state's highest trail race, taking place atop Blue Knob Mountain at over 3,100 feet elevation. The event offers three challenging courses: a 10K "Short Course" featuring steep climbs and technical terrain; a 20K-25K "Mediu..

The Valley View Hard Cider Challenge Half is a scenic and challenging race held at Valley View Farm in Delaplane, VA. Participants can choose from a half marathon, 10k, or 5k course, featuring cross-country, trail, and hill segments. The event offers a festive atmosphere with a finish line cider, fi..

The Final Countdown Tribute is an exciting running event hosted by 2 Lowe Run Company at Amani Brewing in Martinsburg, WV. This unique race features a 1.33-mile loop course where participants must complete laps within a progressively decreasing time limit. Starting with a 20-minute lap, the time sho..