Sykesville
Trail Running Calendar near Sykesville 2026-2027
Explore the top trail runs near Sykesville for 2026-2027! We've gathered 36 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
A 3 mile Reunion Run at Hereford High School as part of the Bull Run Cross Country invitational. The race is open to all ages and carries a $10 registration fee, with registration listed from August 24 to September 26.
A 20 mile supported trail run on the Torrey C. Brown NCR Trail in Freeland, Maryland, offered in both in-person and virtual formats.
October 2026
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.
A scenic 5K at Rocklands Farm Winery with chip timing, on-course aid, awards, post race wine offerings, live music, and race day amenities.
A backyard ultra at Shawan Downs where runners repeat a 4.1667 mile loop each hour until one runner completes a lap alone and is declared the sole finisher.
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.
An 11 mile out-and-back trail race in Cunningham State Park near Thurmont MD with about 2200 ft elevation gain and an aid station at the 5.5 mile turnaround.
Run Through the Grapevine is an 8K cross country race at Linganore Winery in Mount Airy, Maryland on November 8, 2026. The course runs through vineyard rows and adjacent hop yards, and all finishers receive one free winery tasting.
A community fundraiser with a timed 5K, a 1.6K nature walk and a 500 m kids run supporting Toca Juniors Football Club and its Smiles Soccer Program.
Free BRRC GPS 5K at Herring Run Park featuring mixed paved, field and single track terrain, two river crossings, and course variations from local high school routes.
A chip-timed 5 km and 10 km on the flat C&O Canal towpath at Carderock Recreation Area with medal, technical shirt, virtual option and series points.
Celebrate Thanksgiving with a cross country style race through scenic Catonsville. Support the local high school running program with a chip timed 5K or a 1 Mile Family Fun Run for all ages.
A timed trail and paved 5k and 10k at Wheaton Regional Park on November 26 with chip timing, a finisher medal, technical shirt and a virtual option.
A Thanksgiving morning 5K at Eastern Regional Park in Middle River with two laps on mixed paved and natural trails; open to all ages, $15 registration fee.