Trail Running Calendar Maryland 2025-2026

We have found 24 Trailruns in Maryland. Check below where and when you can find the races.

The Mid-Maryland Trail Festival 50k is a trail running event held at Rockburn Branch Park in Elkridge, Maryland. The race covers 31 miles (50 kilometers) through six loops of approximately 5.179 miles each on wooded trails. Participants can run the full 50k solo or form relay teams of 2 to 6 members..

February 2026

The Algonquin 50K is a 50-kilometer trail race held in Pocomoke City, Maryland, at the Pocomoke River State Park. Known as a fast, flat course with minimal elevation change, it offers a mix of single-track and wider horse trails, mostly flat but potentially muddy or sandy depending on weather. The r..

April 2026

Run to Remember in Sykesville, MD, is a multi-distance running event held at Piney Run Park, featuring a scenic 5-mile loop through woods, meadows, and alongside a lake. Participants can choose from a 50K, 25K, 5 Miler, or an 8 Hour Challenge, with the 50K requiring six loops and the 25K three. The..

May 2026

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..