Trail Running calendar near Leonardtown 2025-2026

The Dahlgren Trail Half Marathon is a scenic running event taking place on the Dahlgren Railroad Heritage Trail in King George, Virginia. This half marathon features a flat, out-and-back course that showcases the natural beauty of the area. Participants can enjoy cash prizes, custom finisher medals,..

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 Algonquin 50K is a challenging ultramarathon held in Pocomoke River State Park, Maryland, on the Delmarva Peninsula. The mostly flat, fast course covers about 31 miles on 95% trail, including single-track and horse paths, with sandy sections and possible standing water adding difficulty. The rac..

The Capital Backyard Ultra is a challenging endurance running event held at Meadowood Special Recreation Management Area in Lorton, Virginia, near Washington DC. This Silver Ticket race features a unique format where participants run a 4.167-mile loop every hour, starting on the hour, continuing unt..

The Sheetz-to-Sheetz Trail Run is a 14-mile untimed point-to-point trail run held in King George, Virginia. Starting at a Sheetz convenience store near King George Middle School, the course follows rural roads briefly before transitioning to the flat, well-marked Dahlgren Railroad Heritage Trail, a..

The Bull Run Run (BRR) 50 Miler is a classic 50-mile trail race held annually in Clifton, Virginia, within Hemlock Overlook Regional Park. Established in 1993 and organized by the Virginia Happy Trails Running Club, it is one of the oldest 50-mile races in the U.S. The course features forested, roll..

The Breeze Thru The Trees 5k is a cross-country running event held at Ruppert Nurseries, a 500-acre tree farm located in Gaithersburg, Maryland, within Montgomery County’s Agricultural Reserve. The event features a 5K run and a 1-mile fun run, offering participants a scenic course winding through a..

Run to Remember in Sykesville, MD, is a memorial running event held at Piney Run Park featuring distances of 50K, 25K, 5 miles, and an 8-hour challenge. The course is a scenic 5.25-mile loop through woods and meadows, with about half the route offering lake views. Runners complete multiple loops dep..

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..