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Trail Running Calendar near Sykesville 2026-2027

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Explore the top trail runs near Sykesville for 2026-2027! We've gathered 35 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

November 2026
A free 5K cross country at Herring Run Park on November 15, 2026, with mixed terrain, river crossings, and donations accepted for local scholarships and park support.
A 5k and 10k held on the C&O Canal at Carderock with chip timing, medals, shirts, a virtual option, and proceeds benefiting Project Pink Tax.
A community cross-country event at Catonsville High School with a chip-timed 5K and a 1 Mile Family Fun Run, with all proceeds supporting the CHS cross country program.
A chip-timed 5 km and 10 km on Wheaton Regional Park trails with mixed surfaces, finisher medal, technical shirt, series points, and a virtual option.
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 on the C&O Canal towpath with minimal elevation, race series points, medals and technical shirts.
Trail races of 13.1, 6.55 and 3.1 miles on the Patuxent and Wincopin trails in Columbia, MD; registration includes shirt, medal and knit gloves.
February 2027
Looped trail event at Rockburn Branch Park offering a full 50k (six 5.179 mile loops), relay teams of two to six runners, or single loop options.
Scenic 5k, 10k and half marathon along the Potomac at Great Falls Park with chip timing, finisher medal, technical shirt and a virtual race option.
A 50 km trail race at Hashawha Environmental Center with rolling single-track, stream crossings, five aid stations, and lottery entry opening Jan 1, 2027.
Trail races at Rockburn Branch Park in Elkridge, MD, with 5 mile, 10 mile, and a two person 10 mile relay; registration runs Oct 30 to Dec 4, 2026.
March 2027
An eight hour timed trail run on a 5.5 mile single track loop at Little Bennett Park in Clarksburg, MD on March 6, 2027.
Trail marathon and 50K at Seneca Creek State Park on single track trails, with on-course choice to stop at the marathon or continue to 50K.
Trail race at Codorus State Park with 50K, 25K and 8-mile options on the Ranger Trail; proceeds support a local animal rescue.
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.
Spin in the Woods 2027 is an in person low-key race scheduled for April 10, 2027 and listed on a local running club calendar.
Multirace trail event at Piney Run Park on April 17, 2027 offering 50K, 25K, a 5 Miler and an 8 Hour Challenge with looped course, aid stations, and awards.
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.
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