Sykesville
Trail Running Calendar near Sykesville 2026-2027
Explore the top trail runs near Sykesville for 2026-2027! We've gathered 34 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
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 at Cunningham State Park near Thurmont MD on Catoctin Blue and Cat Rock Yellow trails with one aid station at the 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 free BRRC 5K cross country at Herring Run Park on November 15, 2026, with an XC style start, mixed surfaces, river crossings, and volunteer-supported turns.
A chip timed 5 km and 10 km on the C and O Canal towpath at Carderock Recreation Area with medal, technical shirt, water stations 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.
A timed 5k and 10k at Wheaton Regional Park with mixed-surface out and back courses, medals, chip timing, 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
February 2027
A 31 mile trail event at Rockburn Branch Park in Elkridge, MD featuring a six loop 50K and a relay option for teams up to six people.
Scenic 5k, 10k and half marathon at Great Falls Maryland along the Potomac and C&O Canal, chip timed with medal, shirt and a virtual option.