Baltimore
Trail Running Calendar near Baltimore 2026-2027
Explore the top trail runs near Baltimore for 2026-2027! We've gathered 21 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
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.
Open 6k at Terrapin Nature Park in Stevensville, MD on September 19, 2026; open to all, $25 entry, flat sandy gravel course with bay views.
Annual 5K trail run and family fun run at Terrapin Nature Trail on Maryland's Eastern Shore with a separate 1 mile kids run.
Cancer Warrior 5K on September 26, 2026 raises funds for cancer research with an after party hosted by Independent Brewing and an early registration discount.
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
A 5.25 mile trail race at Gunpowder State Park with a steep opening climb, single-track sections, a fast finish, and race day donation based registration.
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
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.
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 5K and 10K run through Wheaton Regional Park plus virtual options, with points that count toward year-long and fall series standings.
A Thanksgiving morning 5K at Eastern Regional Park in Middle River with two laps on mixed paved and natural trails; open to all ages, $15 registration fee.
December 2026
Eight hour trail endurance race at Terrapin Nature Park where each 2.8 mile lap fills a participant stocking with surprises and top finishers earn awards.
January 2027
5K and 10K races in Stevensville, MD, on varied terrain with forest, sand, Chesapeake Bay Bridge views, and a post-race drink option at a nearby brewery.
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.
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.
50K, 25K, 5 Miler and an 8 Hour Challenge on a 5.25 mile loop at Piney Run Park in Sykesville on April 17, 2027.