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!
February 2027
Trail races around Saint Marys Lake in Leonardtown MD with 50K, 34K and 17K options on a marked 10.5 mile loop and staffed aid stations.
Out-and-back 8k and 16k along the C&O Canal in Great Falls Maryland, chip timed with medals, technical shirts and a virtual participation option.
Trail races at Rockburn Branch Park in Elkridge, MD, with 5 mile, 10 mile, and a two person 10 mile relay; registration runs Oct 30 to Dec 4, 2026.
March 2027
An eight hour timed trail run on a 5.5 mile single track loop at Little Bennett Park in Clarksburg, MD on March 6, 2027.
Trail marathon and 50K at Seneca Creek State Park on single track trails, with on-course choice to stop at the marathon or continue to 50K.
Out and back races at Point of Rocks offering 5K, 10K and half marathon distances with chip timing, finisher medal and a virtual option.
5k and 10k out-and-back races on the C&O canal path near Smoketown Brewery with chip timing, a finisher medal, event shirt, limited water stations, and a virtual option.
HAT Run 50K is a trail ultramarathon in Susquehanna State Park with nearly 4,300 feet of climbing, two 14 mile loops and four stream crossings.
April 2027
Genesee Valley Ultra is a timed loop trail event at Genesee Valley Outdoor Learning Center in Parkton, MD. Runners choose 24 hour, 12 hour, or 6 hour formats to complete as many laps as possible on a 2 mile loop, with chip timing and awards.
A turtle themed 5K at Hopkins Farm Brewery in Havre De Grace raising funds and awareness for the Susquehannock Wildlife Society. The trail race includes wooden participant medals, costume prizes, and an after party with live music.
A 10 hour endurance walking challenge at Wisp Resort on April 10, 2027, offering 7 to 28 mile options with optional weighted rucks and scenic Deep Creek Lake views.
Spin in the Woods 2027 is an in person low-key race scheduled for April 10, 2027 and listed on a local running club calendar.
A chip timed 5K run/walk at Corteau Vineyards on a two lap grass course through the vines, with race swag, a wine pour and proceeds supporting ZERO Prostate Cancer.
A trail event at Piney Run Park featuring a 5.25 mile loop repeated for a 50K, 25K, 5 miler 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 C&O Canal towpath at Carderock with medals, tech shirts, a virtual option, and proceeds benefiting Project Blackbird.
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.
Trail running at the Agricultural History Farm Park in Derwood, Maryland, featuring timed lap Challenges and conventionally timed marathon and 25K races.
Timed 14 hour trail event at Pocomoke YMCA where runners complete 3.3 mile laps on mostly single track terrain with on-course aid and awards for top finishers.