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 scenic cross country 8K at Linganore Winecellars in Mt Airy, MD on November 8, 2026, featuring post race refreshments, awards and live music.
A scenic 5K at Milburn Orchards in Elkton on November 8, 2026, across orchard and farm trails with a portion of proceeds donated to local organizations.
A self timed 5k from Made Me Mine in Abingdon with walking option, stroller friendly course and parking at Constant Friendship Shopping Center.
Trail races in Rosaryville State Park on November 14, 2026 offering 50K and 20K on mostly single track with aid stations, drop bags, and time limits.
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 marathon weekend in Brunswick MD featuring a USATF certified full marathon, a half marathon and a Veterans Challenge 5K along the Potomac and C&O Canal.
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.
Point to point 50.2 miles in Washington County, Maryland, running from Boonsboro along the Appalachian Trail and the C&O Canal to Williamsport.
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.
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.