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Trail Running Calendar near Montgomery County 2026-2027

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Explore the top trail runs near Montgomery County for 2026-2027! We've gathered 69 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

March 2027
Scenic flat half and full marathon in Georgetown along the C&O Canal with chip timing, water stations, a virtual option, and series points.
A trail 5k and 10k at the Winery at Bull Run through Manassas National Battlefield with chip timing, finisher medals, a race shirt, on-course water stations, and proceeds to Manassas Battlefield Trust.
April 2027
A forested 50 mile trail race in Clifton, VA on April 3, 2027, with an accessible course, a 13-hour time limit, and Trail Sisters approval.
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 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.
Multi distance, chip timed races in Georgetown along the C&O Canal featuring medals, technical shirts, water stations, and a virtual option.
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.
USATF certified out and back marathon and half on the flat, unpaved C and O Canal Towpath at Fletcher's Cove with aid stations, finisher medals, and cash awards.
At Burke Lake Park Healthy Strides offers a paved, wheelchair accessible 5K, a 10K trail loop, a kids dash, packet pickup, timing, and finisher medals.
A scenic, flat Mother's Day 5k and 10k in Georgetown DC along the C&O Canal with chip timing, medals, technical shirts, and age group awards.
Trail 5 km and 10 km races at Wheaton Regional Park on May 15, 2027 with chip timing, finisher medals, technical shirts and a virtual race option.
A Georgetown race on the C&O Canal path offering 5k, 10k, and half marathon distances with chip timing, medals, technical shirts, virtual options, and series points.
A chip-timed 5k and half marathon along the C&O Canal in Georgetown with a virtual option, tech shirt, medal, and age-group awards.
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 10K loop trail race at Little Bennett Regional Park in Clarksburg, MD on June 5, 2027, run mainly on single track with hilly and rocky sections.
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