Trail Running calendar near Prince Frederick 2026-2027

A turtle themed 5K at Hopkins Farm Brewery in Havre De Grace raising funds and awareness for the Susquehannock Wildlife Society. The trail race includes wooden participant medals, costume prizes, and an after party with live music.

A memorial running event at Piney Run Park near Sykesville offering 50K, 25K, a 5-mile loop, and an open 8-hour lap challenge with stocked aid stations.

A cross country 5K at Red Shedman Farm Brewery on the Linganore Winecellars grounds, with a technical quarter zip and one pour for finishers and on-site picnic and tasting options.

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.

Trail Demon presents scenic, technical trail races of 5 km and 10 km near Foggy Bottom Road in Bluemont, VA on May 1, 2027, with virtual entry options.

Marathon and half marathon on the C&O Canal Towpath at Fletcher's Cove in Washington DC on May 1, 2027, featuring a mostly crushed gravel out and back course with river views.

A 14 hour timed trail running event at the Pocomoke YMCA where participants complete repeated 3.3 mile laps on mostly single track terrain with aid and awards.

Scenic loop 5K and 10K at Sky Meadows Turners Pond in Delaplane VA with views of fields and streams; virtual options and walkers are welcome.

A 24 hour Backyard ultra on Mason Neck with a 4.167 mile loop, 100 mile limit, single aid station, and a field capped at 100 runners.

A night-time trail event in Prince William Forest Park featuring a 25+ mile loop run twice for 50 miles, with staffed aid stations and park-specific crew and pacer rules.