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.
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.
Scenic 5K through vineyards and farm at Rocklands Farm Winery with chip timing, post run wine options, live music, and awards for overall and age group finishers.
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, Thurmont MD, with a single aid station at 5.5 miles and roughly 2200 feet of elevation gain.
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.
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.
Flat out and back 5k and 10k on the C&O Canal towpath at Carderock Recreation Area on November 22 with walkers welcome and a virtual option.
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.
Scenic 5k and 10k at Wheaton Regional Park with chip timing, a technical shirt and finisher medal, a virtual option, and series points.
A Thanksgiving Day 5K at Eastern Regional Park in Middle River with two laps on mixed paved and natural paths and registration options that include a hat and medal.
December 2026
Timed trail ultra on 12/05/2026 at Little Bennett Regional Park with 5 hour and 9 hour formats, relays, and a 4.5 mile race.
A 13.1 mile out and back on the C&O Canal Towpath at Carderock Recreation Area with online registration, two water stops, live timing, and post-race refreshments.
January 2027
Chip timed 5K, 10K and half marathon along the C&O Canal at Carderock Recreation Area with medals, technical shirts, water stations and series points.