Maryland
Maryland Trail Running Calendar 2026-2027
Explore the best trail runs in Maryland for 2026-2027! Our updated list features 69 exciting trail runs across the region. Find your next trail run in Maryland below and join the trail community at these great events!
May 2027
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 chip timed 5K at Running Hare Vineyards on May 15, 2027 with finisher wine and a stemless glass, race shirts, medals, live music and age group awards.
A 20-mile single-loop hike at Fair Hill NRMA on May 22, 2027, with aid stations, a finisher medal, and roughly 1,600 ft of elevation gain.
Scenic 5K, 10K and half marathon along the Potomac River near Great Falls MD with chip timing, a virtual option, and a partnership with Wounded Warriors in Action Foundation.
June 2027
A backyard ultra in Knoxville Maryland where runners repeat a 4.167 mile loop each hour until one remains; includes a 1 mile Mortals edition and prize money.
A 46th annual memorial five mile run on the C&O Canal Towpath in Williamsport MD with chip timing, awards, and a technical race shirt.
A Juneteenth trail race at Button Farm offering 6k and 12k routes on hilly, scenic Schaeffer Farm Trails with virtual options, chip timing, and finisher medals.
August 2027
Trail races at Bohemia Manor Farm Winery with 5K and 8K courses through vineyards, riverfront and woods, chip timing, awards and a waterfront after party.
Family-friendly mud run with obstacles, mud pits, a pre-party and post-race party at Budds Creek Motocross Park in Mechanicsville on August 28, 2027.