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Trail Running Calendar near Frederick 2026-2027

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Explore the top trail runs near Frederick for 2026-2027! We've gathered 33 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

March 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.
April 2027
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.
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.
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.
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