Trail Running calendar near Leonardtown 2024-2025

We have found 45 Trailruns within 80 miles of Leonardtown. See below where and when you can find the races.

The Chopawamsic Challenge is an exciting 50K and 100K trail race held in Prince William Forest Park, Virginia. This event offers a unique opportunity for runners to test their endurance on scenic trails with significant elevation changes, featuring over 6,000 feet of ascent and descent for the 50K a..

Run to Remember is a commemorative running event held at Piney Run Park in Sykesville, MD, featuring multiple race options including a 50K, 50K Relay, 25K, 5 Miler, and an 8 Hour Challenge. This event honors the memory of cherished members lost, encouraging participants to challenge themselves in th..

May 2025

The Capital Backyard Ultra is a unique endurance running event held in Lorton, Virginia, designed for a maximum of 60 participants. Runners compete on a 4.167-mile loop, starting on the hour, with the goal of being the last runner standing. The event emphasizes camaraderie and support, featuring pro..

June 2025

The OSS/CIA 50 Mile Night Run is a unique trail running event held in Prince William Forest Park, Virginia, which has historical significance as the training ground for OSS spies during World War II. Participants will tackle a challenging 50-mile course consisting of a 25+ mile loop run twice, prima..

August 2025

The MD Heat Trail Race, held at the Patapsco Pickall Area in Elkridge, MD, offers both 25K and 50K trail running options. This event features a challenging course with rolling single track, technical sections, and two river crossings, providing a mix of hiking and running opportunities. Participants..