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Trail Running Calendar near Mount Airy 2026-2027

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Explore the top trail runs near Mount Airy for 2026-2027! We've gathered 40 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

August 2026
Trail race in Elkridge, MD offering 25K and 50K on rolling single track with river crossings, aid stations serving real food, and post-race food and beer.
A 7K trail race at The Woodstock Equestrian Center in Dickerson, Maryland, presented as part of MCRRC's low key series for members. Non member registration has a $20 fee and runs from February 10, 2026 to August 16, 2026.
An evening 4 mile out and back run on the NCR Trail at Paper Mill in Cockeysville, part of the BRRC Grand Prix Series on August 19, 2026.
A 3.8 mile running event at Pen Mar Park that climbs about 1.8 miles to High Rock Overlook and returns to the park. Registered finishers receive an official High Rock Mountain t-shirt and there are early and race day fee options.
September 2026
Cross country at Morven Park with a high school invitational plus an open 5K, featuring food trucks, music and a spectator friendly course.
A 10K road race and a 5K road/trail combo at the Shrine of St Anthony in Clarksville, MD on Sept. 5, 2026. Both USATF certified with chip timing, guaranteed shirts for early registrants, music and family activities.
Races on September 6, 2026 at Carderock Recreation Area in Potomac, MD offering 5K, 10K and Half Marathon courses described as fast and flat with virtual options.
An in-person event on September 26, 2026 in Brunswick, MD featuring a trail-based 5K and timed 3-hour and 6-hour challenges on a 5 mile loop. Proceeds support Brunswick High School Track and Field equipment.
Run On The Rocks in Point Of Rocks, MD on September 26, 2026 features 10 mile, half marathon and 20 mile events. The race is chip timed and includes participant shirts, finisher medals and age group awards.
An annual community 5K run and walk at Agricultural History Farm Park in Derwood, Maryland on September 27, 2026, organized by MD District 15 Democratic Caucus. Offers adult and youth entries plus a free youth option with an accompanying adult.
October 2026
A community charity race in Gaithersburg on October 3, 2026, featuring cross-country 10K and 5K, a paved 1-mile accessible fun run, and a kids Trike-A-Thon. Proceeds support Comfort Cases and Covenant Life School and include a post-race backpack-pack..
A trail 5K at Claude Moore Park in Sterling VA on October 3, 2026, offering in-person and virtual entries with medal and shirt options.
Experience a unique trail event at Milkhouse Brewery in Mount Airy featuring a 5 mile race and timed ultra challenges. Complete as many loops as possible over four or eight hours on this scenic farm course.
A community trail event on October 11, 2026 at Bretton Woods Recreation Center in Darnestown, MD offering a 5K trail run and a 1 mile walk. The event raises funds and awareness for addiction prevention, education, and support.
Participate in a 10 km run through the scenic Black Hill Regional Park in Boyds. This low key event offers a straightforward racing experience for both club members and the general public in a natural park setting.
Trail ultramarathon in Patapsco Valley State Park offering 50k and 25k options, in-person and virtual, with aid stations, event shirt, and finisher awards.
Scenic 5K through vineyard and farm at Rocklands Farm Winery with chip timing, age group awards, and a post-race wine tasting with live music. Walkers and children are welcome and a one hour course time limit applies.
5th Annual Mackyard Ultra is a race by the Baltimore Road Runners Club on October 31 at Shawan Downs in Cockeysville, MD with a $20 entry fee and a 100 runner limit.
November 2026
Experience a mix of twisty singletrack and open farm field running in Germantown. This late autumn trail event offers three distances and a festive post race atmosphere at the historic Button Farm.
Experience a 50 mile trail race through the scenic Seneca Greenway and Muddy Branch trails in Maryland. This event features forested single track terrain and small stream crossings for dedicated distance runners.
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