Trail Running calendar near Mechanicsville 2026-2027

Run to Remember in Sykesville uses a 5.25 mile loop at Piney Run Park for 50K, 25K, a 5 miler and an 8 hour challenge. Fees include park entrance, a custom ice bandana and a commemorative mug.

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 100 mile ultramarathon on the C&O Canal towpath in Knoxville, MD with start and finish at Camp Manidokan. The course is one 40 mile loop plus two 30 mile loops, with multiple aid stations and extensive riverside scenery.

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 5k & 10k in Bluemont VA features scenic, hilly trail courses with technical terrain around the property; runners can enter in-person 5 km or 10 km races or choose virtual options with medal or shirt.

Flat marathon and half marathon along the C&O Canal Towpath at Fletcher's Cove in Washington, DC. The mostly crushed gravel out and back course offers shaded river views, aid stations, and monetary prizes for top finishers.

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

Backyard-style ultra in Knoxville MD with repeating 4.167 mile laps every hour until one remains, plus a concurrent 1 mile Mortals edition.