Maryland
Maryland Trail Running Calendar 2026-2027
Explore the best trail runs in Maryland for 2026-2027! Our updated list features 67 exciting trail runs across the region. Find your next trail run in Maryland below and join the trail community at these great events!
April 2027
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 race along the C&O Canal towpath near Knoxville MD with a 40 mile loop plus two 30 mile loops, multiple aid stations, and a Camp Manidokan start.
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 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.
A morning 5K held as part of the Fair Hill Scottish Games on May 15, 2027, in Elkton, MD, with on-field entries accepted, an entry fee that includes admission, and cash prizes plus trophies for top finishers.
A 20 mile loop through Fair Hill Natural Resources Area on May 22, 2027 with aid stations, a finisher medal and complimentary on site parking.
June 2027
Backyard-style ultra in Knoxville MD with repeating 4.167 mile laps every hour until one remains, plus a concurrent 1 mile Mortals edition.