Maryland
Maryland Trail Running Calendar 2026-2027
Explore the best trail runs in Maryland for 2026-2027! Our updated list features 69 exciting trail runs across the region. Find your next trail run in Maryland below and join the trail community at these great events!
November 2026
A self-timed 5 miles loop in Bel Air that starts and finishes at Southampton Middle School and follows part of the Bel Air Town Run Course.
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 trail and canal run near Great Falls, Maryland on November 26, 2026 covering about 10 miles with options to shorten. Entry opens November 12 and is capped at 29 runners; entrants receive course instructions before the run.
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.
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 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.
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 club 5 km run and walk on the new section of the Ma and Pa Trail from North Avenue Trailhead in Bel Air with self-timing and on-site merchandise.
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
Multi-distance race on the C&O Canal Trail at Williamsport Park with chip timing, finisher medal, technical shirt, virtual option, and series points.
Experience the rolling hills of Fair Hill Natural Resource Management Area during this winter trail event. Choose between 25K or 50K distances on beautiful single track trails with heated facilities and fully stocked aid stations.
Chip timed 5K, 10K and half marathon on the C&O Canal towpath with minimal elevation, race series points, medals and technical shirts.
Gravel-trail 5K and 10K at Terrapin Nature Park on January 23, 2027, with chip timing, water views, series points, and a post-race drink at Cult Classic Brewing.
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 trail 5K on February 20, 2027 at the Wicomico Ranger Station in Parsonsburg, MD that raises funds for 4STEPS therapeutic riding programs, with age/gender prizes in Amazon gift cards and a $32 registration fee.
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.