Trail Running calendar near Leonardtown 2026-2027

We have found 89 Trailruns within 80 miles of Leonardtown. See below where and when you can find the races.

A half marathon and a 5K at Harwoods Mill Park in Yorktown on January 17, 2026, with shuttle parking from McReynolds Athletic Complex. Limited fields, four aid stations, on-site packet pick-up and specific trail conditions.

February 2027

A trail 5K on February 20, 2027 at the Wicomico Ranger Station in Parsonsburg, MD that raises funds for 4STEPS therapeutic riding programs, with age/gender prizes in Amazon gift cards and a $32 registration fee.

March 2027

Test your limits in Lorton at this elite backyard marathon featuring dedicated day and night loops. With a limited field of 65 runners and a chef supported aid station, it is the perfect venue for a personal best.

April 2027

A 14 mile untimed point to point trail run along the Dahlgren Railroad Heritage Trail that starts at one Sheetz and finishes at another. The event features unusual aid station snacks and practical finisher swag.

A 50 mile trail race near Clifton, Virginia on April 4, 2027, run over forested, rolling terrain in spring. Entry opens October 1, 2026; the race has a 13-hour limit and a $125 entry fee.

A trail event at Piney Run Park in Sykesville using a 5.25 mile loop for 50K, 25K, 5 mile and an 8 hour challenge. Aid stations, commemorative mug and ice bandana included; portions of proceeds support charity.

May 2027

A trail running event at the Agricultural History Farm Park in Derwood, Maryland, featuring lap based 3, 6, and 10 hour Challenges and a conventionally timed marathon and 25K. Volunteers receive the same finishers' swag.

A trail run of about 10k that features roots, gravel, rough terrain and low hanging branches. Water stops are self serve and participants must bring their own hydration; wave starts are used to manage trail volume.

A 24 hour Backyard-format ultrarun near Lorton, Virginia using hourly 4.167 mile loops with a 100 mile limit. One central aid station beneath a horse pavilion supplies water, Gatorade and snacks while crews are allowed only at that station.

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