Trail Running calendar near Leonardtown 2025-2026

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 50 is a trail race of 50 miles scheduled for April 4, 2026, in Clifton, Virginia. The event is organized by volunteers from the Virginia Happy Trails Running Club and was established in 1993. The listed entry fee is $125 and a 13 hour time limit applies. Registration is planned to..

The Molon Lave 5k is a scenic cross-country running event held at Molon Lave Winery in Warrenton, Virginia. The course features three loops around the winery property, offering a fairly flat terrain with natural vineyard surroundings. Walkers are welcome, and a virtual race option is available for r..

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..

April 18, 2026, Sip & Stride 5k & 10k returns to Southern Revere Cellars in Louisa, Virginia, for a winery-style cross-country race. The 5k is two laps and the 10k four laps around the winery property, featuring mostly flat terrain with no major hills. Seven water stations along the 10k and three on..

Run to Remember in Sykesville, Maryland takes place at Piney Run Park (30 Martz Rd, Sykesville, MD 21784). The event offers multiple distances: 50K (6 loops of 5.25 miles), 25K (3 loops), an 8 Hour Challenge, and a 5.25-mile race. The course runs through woods and meadows with lake views along about..

Farm Park Challenge is a trail running event at Agricultural History Farm Park in Montgomery County, Maryland, presented by My Muddy Shoes. The race offers multi-hour lap formats: 3-Hour, 6-Hour, and 10-Hour challenges, totaling 3, 6, or 10 laps, each start at the top of the hour and must be complet..

The OSS/CIA 50 Mile Night Run is a challenging ultramarathon held in Prince William Forest Park, Virginia, a historic site once used to train World War II OSS spies. The race features a 25+ mile loop primarily on single-track trails, fire roads, and several bridge and road crossings, which runners c..

The 3H Trail Half Marathon + DHRT 50K is scheduled for Saturday, August 8, 2026, in King George, VA (4224 University Drive, 22485). The event features two races: 3H Trail Half Marathon Dahlgren Heritage Rail Trail 50K Registration opens October 1, 2025. The half marathon fee is listed at $65 and..

Halloween Horror 5k & 10k returns to Conway Robinson State Forest Park in Gainesville, VA, offering a forest trail race with a Halloween theme. The event features 5k and 10k distances, with the 10k being two laps of the 5k course. The loop route traverses forest trails with technical sections and mi..