Maryland
Maryland Trail Running Calendar 2026-2027
Explore the best trail runs in Maryland for 2026-2027! Our updated list features 70 exciting trail runs across the region. Find your next trail run in Maryland below and join the trail community at these great events!
October 2026
Celebrate Halloween with a nighttime 5K trail race through the woods of Salisbury featuring a decorated course and costume awards.
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
Trail races of 50K and 25K take place in Little Orleans MD on November 1, 2026 with aid stations and official finish cutoffs.
Enjoy a 5k run or walk from the lighthouse at Concord Point Park as part of the Harford County Running Club Sunday Run Series.
Experience a mix of twisty singletrack and open farm field running in Germantown. This late autumn trail event offers three distances and a festive post race atmosphere at the historic Button Farm.
Experience a 50 mile trail race through the scenic Seneca Greenway and Muddy Branch trails in Maryland. This event features forested single track terrain and small stream crossings for dedicated distance runners.
A community fundraising run in Cumberland along the GAP Trail offering 10K, 5K and a 1K fun run, with team results and scholarships for students.
A benefit run and walk along the Patuxent River supporting conservation, with USATF-certified 5K and 10K courses and a 3K fun walk.
An 11 mile out and back trail race at Cunningham State Park near Thurmont MD on Catoctin Blue and Cat Rock Yellow trails with one aid station at the turnaround.
Trail 5k and 10k at Rock Creek Regional Park supporting The Rock Creek Foundation, with chip timing, medals, shirts, a virtual option, and series points.
An annual cross-country 8K at Linganore Winecellars in Mt Airy with a course through the winery grounds, post-race refreshments, awards, and a sweatshirt premium.
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 BRRC 5K cross country at Herring Run Park on November 15, 2026, with an XC style start, mixed surfaces, river crossings, and volunteer-supported turns.
A 5 km on the Mason-Dixon Trail in Darlington with two multi-loop challenge options and self-timed results, free registration.
25K trail race in Queen Anne, MD on November 21, 2026 with mostly single track, three stocked aid stations, awards for top finishers, and no refunds if canceled.