Maryland
Maryland Trail Running Calendar 2026-2027
Explore the best trail runs in Maryland for 2026-2027! Our updated list features 65 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
Trail races in Rosaryville State Park offering 50K and 20K on mostly single track loops through woods and meadows with aid stations and drop bag support.
A Thanksgiving themed 5 km run at Big Cork Vineyards in Rohrersville, Maryland, on November 14, 2026. The event is timed by J3 Timing and includes a t shirt, collapsible wine glass, finisher medal, and a wine pour.
A fall running weekend in Brunswick, MD, featuring towpath marathon and half marathon routes plus a Veterans Challenge 5K through historic neighborhoods.
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 5 km on the Mason-Dixon Trail in Darlington with two multi-loop challenge options and self-timed results, free registration.
A point to point 50.2 mile ultramarathon in Washington County, Maryland held every November since 1963, with Appalachian Trail, C&O Canal towpath, aid stations and GPS tracking.
A trail 25K in Queen Anne, MD on Nov 21, 2026 featuring mostly single-track terrain, three aid stations, and awards for the top three men and women.
A small, capped fall race on the C&O Canal towpath at Great Falls Tavern offering a half marathon, 10K and family friendly 5K with chip timing and live tracking.
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 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.
Club trail run near Great Falls on Nov 26, 2026, about 10 miles along trails and the C&O Canal with limited entry and no on course medical support.
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.