Trail Running calendar near Winchester 2026-2027

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.

UltraTrax Massanutten is a single day endurance walk in Massanutten, VA offering 7, 14, 21 and 28 mile options with a 10 hour finish window, optional ruck weights, and an advanced ridgeline segment available in safe weather.

C&O Canal 100 is a 100 mile ultramarathon along the C&O Canal towpath in Knoxville, MD on April 24, 2027. The course uses one approximately 40 mile loop and two approximately 30 mile loops with multiple aid stations and volunteer support.

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 Backyard ultra on Mason Neck with hourly 4.167-mile loops and a 24 hour, 100-mile limit. The course runs on bridle trails with one central aid station offering water, ice, Gatorade and snacks.