Westminster
Trail Running Calendar near Westminster 2026-2027
Explore the top trail runs near Westminster for 2026-2027! We've gathered 22 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 Halloween themed 5K at Adams County Winery on October 25, 2026, with chip timing, online results, and registration perks including a tee, wine glass, and finisher medal.
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
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.
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.
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.
January 2027
February 2027
A 50 km trail run at Hashawha Environmental Center in Westminster MD, featuring varied single-track, open fields, stream crossings and 5 aid stations. Entry for 2027 uses a lottery opening January 1, with indoor facilities and hot post-race food.
March 2027
An eight hour timed trail ultrarun on a 5.5 mile single track loop at Little Bennett Park near Clarksburg, MD. Registration opens Oct 1, 2026.
April 2027
Genesee Valley Ultra is a timed loop trail event at Genesee Valley Outdoor Learning Center in Parkton, MD. Runners choose 24 hour, 12 hour, or 6 hour formats to complete as many laps as possible on a 2 mile loop, with chip timing and awards.
Experience a scenic loop course through the woods and meadows of Piney Run Park with distances ranging from a 5 miler to a 50K and an 8 hour challenge.
A cross country 5K at Red Shedman Farm Brewery on the Linganore Winecellars grounds, with a technical quarter zip and one pour for finishers and on-site picnic and tasting options.