Trail Running calendar near Leonardtown 2025-2026

We have found 77 Trailruns within 80 miles of Leonardtown. See below where and when you can find the races.

The Angela Ivory Memorial Runs is an annual running event held at Killen's Pond State Park in Felton, DE, featuring a 50K, 24-hour, and 100-mile race. The course consists of a 3.10-mile dirt loop that is relatively gentle and accessible for runners. This event emphasizes a self-supported, community-..

February 2025

The ICY-8 event in Spotsylvania, VA, is an exciting trail running competition that features an 8-hour adventure trail run and a new HALF MARATHON+ option. Set against the scenic backdrop of Lake Anna State Park, participants can choose from various loop courses, including 8.0 miles, 4.7 miles, and a..

The Great Frosty Forest Marathon, taking place on February 2, 2025, offers a range of running events including a 5k, 10k, half marathon, and full marathon, all set in the scenic Prince William Forest Park. Participants can earn points towards various year-long series and enjoy a chip-timed experienc..

The Little Patuxent River Half Marathon & 10K is a scenic running event held in Columbia, Maryland, featuring a half marathon (13.1 miles), a 10K (6.55 miles), and a new 5K option. The race takes place on the beautiful Patuxent and Wincopin trails, offering a manageable terrain suitable for both beg..

The Delmarva Ultra Challenge (DUC) is a unique 100K trail race designed for those seeking an intense challenge. Participants run two back-to-back 50K races: the first takes place at an undisclosed location on Friday night, followed by the traditional Algonquin race course on Saturday morning. The co..

The Algonquin 50K is a trail running event taking place in Pocomoke City, MD, on February 8, 2025. This race offers a flat, fast course ideal for both first-time ultra runners and seasoned participants looking to achieve a personal best. The course is primarily composed of trails, with well-stocked ..

The Froggy Hollow 5 & 9, presented by Altra, is a timed trail ultra event taking place at Little Bennett Regional Park in Clarksburg, MD. Participants can choose from various challenges, including a 5-Hour Challenge, 9-Hour Challenge, and relay options. The course features a scenic 4.3-mile loop, wi..

The Super Bowl Trail Race is a unique 7-mile running event held in Cromwell Valley Park, Baltimore, MD, on Super Bowl Sunday. Participants can enjoy scenic trails featuring rolling hills, fire roads, and single-track paths, culminating in a fast downhill finish. The race promotes fitness while suppo..

The Manassas Battlefield Trust 10k is a scenic running event taking place at the historic Manassas National Battlefield, with the start and finish at The Winery at Bull Run. Participants can enjoy a trail run that includes cross-country paths, dirt trails, and boardwalks, while also earning points t..

The Dahlgren Trail Half Marathon is a scenic running event taking place on February 15, 2025, along the 16-mile Dahlgren Railroad Heritage Trail in King George County, Virginia. This flat, out-and-back course offers participants a chance to enjoy the natural beauty of the area while competing for ca..

The Saint Marys Lake Trail Series is an exciting running event taking place in Leonardtown, MD, featuring three race distances: 50K, 34K, and 17K. Set against the scenic backdrop of Saint Mary’s Lake and the surrounding Salem Forest, participants will navigate a roughly 10.5-mile loop that combines ..

March 2025

The Dark Side 8 Hour Ultra is an annual trail running event held at Little Bennett Park in Clarksburg, MD. Participants can run as many laps as they wish on a scenic 5.5-mile loop, primarily on single track trails. This timed event encourages runners to enjoy the outdoors as spring approaches. The r..

The Paradise Springs 10k is a challenging trail running event held at Hemlock Overlook Park, featuring a scenic course with significant elevation changes and technical sections. Participants can enjoy a glass of wine from Paradise Springs Winery post-race, along with a finisher medal and a technical..

The Spring Backyard Burn Trail Run at Wakefield Park is part of a series of trail running races in Northern Virginia, featuring 5 and 10-mile courses. Set in a scenic location near the Capital Beltway, the event offers a mix of single-track hiking trails, doubletrack paths, and shallow stream crossi..

The Bigfoot Endurance 5 & 10 Mile Trail Race takes place at Rockburn Branch Park in Elkridge, Maryland. Participants can choose between a 5-mile run, a 10-mile run, or a 2-person relay for the 10-mile distance. The terrain is designed to be easy to moderate, making it suitable for both novice and ex..

The Robious Landing 3 Miler is a trail running event taking place at Robious Landing Park in Midlothian, Virginia. Scheduled for March 2, 2025, the event features both an in-person race and a virtual option, allowing participants to run at their convenience from March 1 to March 3. This race emphasi..

The Running Ravens 5k is a fundraising event scheduled from March 7 to March 10, 2025, in Chester, Virginia. Participants can choose to run the 5k in person or opt for a virtual race. The course will traverse a cross-country trail, which is not suitable for strollers, dogs, or wheelchairs. Registrat..

The MCRRC Seneca Creek Greenway Trail Marathon & 50K is a running event scheduled for March 8, 2025, in Gaithersburg, Maryland. Participants can choose between a marathon and a 50K race, making it suitable for various levels of endurance runners. The event is organized by the Montgomery County Road ..

The Perfect Day 50K is an exciting endurance running event held at Massanutten's Western Slopes, where participants run a 5K every hour for 10 hours. This unique challenge allows individuals and teams to compete, with options for alternating loops or completing consecutive hours. The course features..

The Last Stand Loch Lothian Backyard Ultra is an exciting endurance event set to take place in Midlothian, Virginia. This unique race challenges participants to complete a 4.18-mile loop within one hour, with the goal of being the last runner standing. The event is designed for both seasoned ultra-r..