Sykesville
Trail Running Calendar near Sykesville 2026-2027
Explore the top trail runs near Sykesville 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.
September 2026
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.
Fast, flat 5K, 10K and half marathon at Carderock Recreation Area on September 6, 2026, with virtual options and walkers welcome.
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
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..
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.
Scenic 5K at Rocklands Farm Winery featuring cross country style trails, chip timing, age group awards, postrace wine tasting and family friendly 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.
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 event on November 8, 2026 offering a 5K, a 1.6K nature walk, and a kids 500 m run with proceeds supporting the Toca Juniors Football Club.
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 Thanksgiving weekend run at Carderock Park on the Chesapeake and Ohio Canal Towpath offering in person 5K and 10K races and virtual entries.
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 5K and 10K run through Wheaton Regional Park plus virtual options, with points that count toward year-long and fall series standings.