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Trail Running Calendar near Westminster 2026-2027

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Explore the top trail runs near Westminster for 2026-2027! We've gathered 24 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

August 2026
Trail race in Gunpowder Falls State Park on August 9 with one or two mostly single-track loops of 4 or 8 miles and race-morning registration only.
Trail race in Elkridge, MD offering 25K and 50K on rolling single track with river crossings, aid stations serving real food, and post-race food and beer.
A trail 5K in Gettysburg on August 15, 2026, with a race shirt option for early registrants and an event bottle opener medal. Brewfest options and tours of the Daniel Lady Farm House and Barn are available the same day.
An evening 4 mile out and back run on the NCR Trail at Paper Mill in Cockeysville, part of the BRRC Grand Prix Series on August 19, 2026.
A memorial 5K trail run at Genesee Valley Outdoor Learning Center in Parkton, MD, with a 5K, 1-mile walk, kids dash, team entries, and an In Spirit donation option. Proceeds support a scholarship fund and a post-race festival offers food and music.
A 3.8 mile running event at Pen Mar Park that climbs about 1.8 miles to High Rock Overlook and returns to the park. Registered finishers receive an official High Rock Mountain t-shirt and there are early and race day fee options.
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.
A chip timed trail race at South Branch Farms offering 5K and 10K routes on varied terrain with creek crossings, climbs, wildlife sightings, and a post race gathering. Proceeds support the Farm and Natural Lands Trust of York County.
Trail event at Codorus State Park offering a 40 Mile Ultra, a 40 Mile Relay, and a 25K on looped trails with stocked aid stations and nearby camping.
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.
Experience a supported long distance run on the hardpacked dirt and gravel of the Torrey C. Brown Trail. This twenty mile event serves as an ideal training opportunity for those preparing for a fall marathon.
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.
Trail ultramarathon in Patapsco Valley State Park offering 50k and 25k options, in-person and virtual, with aid stations, event shirt, and finisher awards.
5th Annual Mackyard Ultra is a race by the Baltimore Road Runners Club on October 31 at Shawan Downs in Cockeysville, MD with a $20 entry fee and a 100 runner limit.
November 2026
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 5K cross country at Herring Run Park on November 15 featuring mixed surfaces, two river crossings, wooded trails, and donations accepted for local scholarships and park support.
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.
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.
Club-based 10-mile competition at Howard Community College where runners score points for RRCA clubs, with awards by club and a 2h10m cutoff.
March 2027
An annual eight-hour timed trail event at Little Bennett Park near Clarksburg, MD, run on a mainly single-track 5.5 mile loop.
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