Baltimore
Trail Running Calendar near Baltimore 2026-2027
Explore the top trail runs near Baltimore for 2026-2027! We've gathered 19 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A 5.25 mile trail race at Gunpowder State Park on October 18, 2026 featuring a steep opening climb, single track sections, downhill stretches, and donation based entry.
A 5K walk and run on October 18, 2026 at the Ma and Pa Trail Williams St trailhead in Bel Air, MD; registration $20 from Sept 26 to Oct 15 and finishers receive a Husky 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
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.
Scenic 5k and 10k at Wheaton Regional Park with chip timing, a technical shirt and finisher medal, 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
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.
A 15K trail race at Quiet Waters Park in Annapolis on December 13, 2026, part of the Championship Series with special rates for Striders members and race day registration.
A community New Year's Eve event in Bel Air offering a self-timed 5K at Cedar Lane Park with a family countdown and a sparkling cider toast after the run.
January 2027
Scenic gravel 5k and 10k at Terrapin Nature Park with chip timing, finisher medal, virtual option, and a drink ticket for Cult Classic Brewing.
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.
Memorial multi-distance event at Piney Run Park in Sykesville with a 5.25 mile loop, aid stations, commemorative posters, 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.