Trail Running calendar near Winchester 2025-2026

The Schaeffer Half Marathon and 10K Trail Run, hosted by EX2 Adventures, takes place at the scenic Button Farm in Germantown, Maryland. This event features two distances: a 13.3-mile half marathon and a 6.7-mile 10K+, both offering challenging courses with twisty singletrack trails and wide-open far..

The Rosaryville Veterans Day Trail Race, hosted by Annapolis Striders, is an annual trail running event held at Rosaryville State Park in Upper Marlboro, Maryland. The 16th edition in 2025 features two distances: a 50K and a 20K race. Both courses wind through scenic wooded trails and meadows, prima..

The Fall Backyard Burn Trail Run at Hemlock Overlook in Clifton, VA, is a scenic trail running event featuring 5-mile and 10-mile race options. Set in a 425-acre park along the historic Bull Run, the course offers a mix of hiking trails, old dirt roads, stream crossings, grassy fields, and minimal p..

The Fall Backyard Burn at Laurel Hill is a trail running event held at the Workhouse Arts Center in Lorton, VA, set within 1,600 acres of scenic former prison grounds. The course features a mix of forested and open meadow singletrack trails, primarily dirt and crushed stone, with minimal pavement an..

The Winery at Bull Run Turkey Trot is a scenic trail run held at the Manassas National Battlefield, featuring 5k and 10k options. Participants enjoy running through historic Civil War sites on dirt trails, cross-country paths, and gravel terrain, with some hills along the course. The event benefits..

The 21st Annual Catonsville High School XC Turkey Trot is a cherished community event celebrating health and wellness. Scheduled for November 27, 2025, this event features a 1 Mile Family Fun Run and a 5K race, both of which are chip-timed. Participants can enjoy a family-friendly atmosphere while s..

The Lake Anna Turkey Trot Half is a scenic and challenging race held at Lake Anna State Park, featuring a half marathon, 10k, and 5k courses. The half marathon is an out-and-back trail race with a 3-hour and 15-minute time limit, while the 10k and 5k courses combine trail and paved roads. Participan..

Devil Dog Ultras is a challenging trail running event held in Prince William Forest Park near Triangle, Virginia. It offers three race distances: 100 miles, 100K, and 50K, all run on a loop course featuring primarily single-track trails with some roots, rocks, and rolling hills but no major climbs...

The Fall Backyard Burn Trail Run at Fountainhead Regional Park in Fairfax Station, VA, is a popular trail running event held annually, with the 2025 race scheduled for December 7. The course features scenic hiking trails and old dirt roads along the Occoquan Reservoir, offering two distance options:..

The Mid-Maryland Trail Festival 50k is a trail running event held at Rockburn Branch Park in Elkridge, Maryland. The race covers 31 miles (50 kilometers) through six loops of approximately 5.179 miles each on wooded trails. Participants can run the full 50k solo or form relay teams of 2 to 6 members..

The ICY-8 Spotsylvania Courthouse is an endurance trail running event held at Lake Anna State Park in Spotsylvania, Virginia. Featuring an 8-hour adventure trail run and a new half marathon+ option, the event offers a figure-8 course composed of three loops: an 8.0-mile long loop, a 4.7-mile loop, a..

The Bull Run Run (BRR) 50 Miler is a historic trail race held in Clifton, Virginia, organized by the Virginia Happy Trails Running Club. Established in 1993, it is one of the oldest 50-mile races in the U.S. The course traverses forested, rolling terrain along the Bull Run Occoquan Trail, showcasing..

Run to Remember in Sykesville, MD, is a multi-distance running event held at Piney Run Park, featuring a scenic 5-mile loop through woods, meadows, and alongside a lake. Participants can choose from a 50K, 25K, 5 Miler, or an 8 Hour Challenge, with the 50K requiring six loops and the 25K three. The..

The Farm Park Challenge is a unique trail running event hosted by My Muddy Shoes at the Agricultural History Farm Park in Montgomery County, Maryland. Participants can choose from three timed challenges—3-hour, 6-hour, or 10-hour—where runners must complete one lap of the course each hour, resting o..