Trail Running calendar near Leonardtown 2025-2026

The Ripper - Sunrise to Sunset is a unique 14-hour and 6-minute timed trail running event held at the Pocomoke YMCA in Pocomoke, Maryland. Participants run a challenging 3.75-mile loop course, primarily single-track trails with rolling hills and rooty terrain, repeating as many laps as possible from..

The Dahlgren Trailblazer is an annual community bike event held in King George, Virginia. Participants embark on a friendly 8-mile ride starting from the trailhead at 10431 Bloomsbury Road, turning around at 9274 Comorn Road. The event is organized by the Friends of the Dahlgren Railroad Heritage Tr..

The Dominion Energy Riverrock Trail Running Events, taking place from May 16 to May 18, 2025, in Richmond, VA, features a variety of races including the Belle Isle Blitz (5k), James River Scramble (10k), and Bust the Banks Half Marathon. This outdoor sports festival, organized by Sports Backers and..

The Fountainhead Half Marathon and 10K Trail Run takes place at Fountainhead Regional Park in Fairfax Station, Virginia, just 30 minutes from Washington D.C. This challenging event features a half marathon of approximately 13.5 miles and a 10K of about 7.2 miles, both on rugged trails with rocks, ro..

The Night Raider 10k and 5k is a scenic trail run held at the Manassas National Battlefield, starting and ending at The Winery at Bull Run in Centreville, VA. Participants can enjoy a course that includes cross-country paths, dirt trails, a boardwalk, and gravel sections, with some hills. The event..

The Happy Tail Wine Trail 5k is a fun and inclusive running event held at 53rd Winery in Louisa, Virginia. Participants can enjoy a scenic cross-country course around vineyards, with options for a 5k race, a 1-mile fun run for children aged 5-13, and a dog jog for furry friends. The event promotes c..

The Capital Backyard Ultra is an endurance running event held in Lorton, Virginia, featuring a unique format where participants run a 4.167-mile loop every hour until only one runner remains. The race supports experienced backyard ultrarunners aiming to push their limits, with a maximum of 60 partic..

The Taskinas Creek Half Marathon, set in York River State Park, Williamsburg, VA, offers a unique trail running experience. Scheduled for June 1, 2025, this event features a challenging course that includes single track trails, fire roads, and a short road section, with a time limit of 4.5 hours. Re..

The Dash Through the Dirt event offers 5k, 10k, and half-marathon races at Carderock Recreation Area in Potomac, MD. The courses run along the scenic C&O Canal Towpath, featuring light gravel trails with minimal elevation changes, ideal for personal records. Participants receive a finisher’s coin, t..

The OSS/CIA 50 Mile Night Run is a challenging ultramarathon held in Prince William Forest Park, Virginia, known for its historical ties to the U.S. intelligence community. The race features a 50-mile course primarily on single-track trails, with some fire roads and crossings, run twice to complete..

The Last Stand Army Backyard Ultra is a challenging endurance race held in Midlothian, Virginia, on Flag Day, June 14, 2025, to honor the 250th Birthday of the U.S. Army. Participants run a 4.167-mile loop every hour on the hour, continuing until only one runner remains to complete a final loop.The..

The Juneteenth Menare Foundation 12k & 6k is a scenic trail race held at Button Farm in Germantown, Maryland, celebrating Juneteenth. Participants can choose between a challenging 12k or a 6k course through the Schaeffer Farm Trails, with scenic and hilly terrain. The event features chip-timed resul..

The Blue Crab Bolt Trail Run at Seneca Creek State Park in Gaithersburg, MD, is the opening race of the 14th annual Blue Crab Bolt Trail Running Series. Scheduled for June 21, 2025, it offers two trail race distances: approximately 5K (3.3 miles) with 200 feet elevation gain and 10K (6.4 miles) with..

The Night Owl 9K is a challenging trail race held at Freedom Park in Williamsburg, Virginia. The 9-kilometer course features a mix of single track, fire road, and paved trails with rolling hills and technical sections including roots and twists, offering a mountain bike trail-like experience. The ra..

The 53rd Winery 5k & 10k is a scenic cross-country race held at 53rd Winery in Louisa, Virginia. Participants can choose between a 5k or 10k course, which loops around vineyards and winery grounds. The event features chip-timed races, finisher medals, technical shirts, and a complimentary glass of w..

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 Endless Summer 6-Hour Run is an annual endurance event held in Annapolis, Maryland, organized by the Annapolis Striders. Participants run for six hours on a 2.5-mile loop course that offers scenic views of Chesapeake Bay and the Bay Bridge. The event supports the Semper Fi Fund, with a portion o..

The Murderkill Ultramarathon is an exciting running event held at Killen's Pond State Park in Felton, Delaware. Participants can choose from three race options: a 50-mile, a 50K, or a 12-hour challenge, all set on a scenic 3.1-mile dirt loop trail. The course features a mix of shaded paths and gentl..

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 for the longer course). The race takes place on well-maintained, flowy, and fast trails that include twisty single-track sections, stream crossings, log ramps..

The Blue Crab Bolt Trail Run at Little Bennett is a scenic trail running event held in Little Bennett Regional Park, Clarksburg, Maryland, a 3,600-acre park featuring over 20 miles of trails, streams, and camping areas. The race offers two distances: a 5K+ (3.7 miles) course, which is beginner-frien..