Maryland
Maryland Trail Running Calendar 2026-2027
Explore the best trail runs in Maryland for 2026-2027! Our updated list features 74 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 timed mountain trek at Wisp Resort offering 7, 14, 21, and 28 mile loop options with a 10 hour limit; well marked trails, optional weighted vests for bonus swag, and finishers receive a shirt, patch, and medal.
5K run and 1.5 mile walk at Corteau Vineyards in Mechanicsville, MD on April 11, 2027, timed and scored by J3 Timing.
Experience a scenic loop course through the woods and meadows of Piney Run Park with distances ranging from a 5 miler to a 50K and an 8 hour challenge.
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 on the scenic C&O Canal with an almost entirely flat course, starting and finishing at Camp Manidokan near Knoxville, Maryland, Apr 24 and 25 2027.
Chip-timed 5k, 10k and half marathon on the flat C&O Canal towpath at Carderock, with technical shirts, medals, water stations and a virtual race option.
May 2027
MoCo CARES Charity Race in Gaithersburg, MD features 10K and 5K cross country courses, a paved 1 mile fun run, and a kids Trike-A-Thon supporting Comfort Cases and Covenant Life School.
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.
Test your endurance at The Ripper, a 14 hour timed race on a 3.3 mile trail loop in Pocomoke where runners complete as many laps as possible from sunrise to sunset.
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.
Hike a scenic 20 mile loop through the woodlands and fields of Fair Hill Natural Resources Management Area in Maryland.
Scenic 5k, 10k and half marathon at Great Falls, MD along the Potomac and C&O Canal with chip timing, medals and a virtual option.
June 2027
A backyard ultra in Knoxville MD where runners repeat a 4.167 mile loop each hour until one remains; a parallel 1 mile Mortals Edition runs under the same rules.
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.