Maryland
Maryland Trail Running Calendar 2026-2027
Explore the best trail runs in Maryland for 2026-2027! Our updated list features 73 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
Trail event at Patapsco Valley State Park offering 50k and 25k distances with on-site and virtual options, aid stations, shirts, and distinct finishers awards.
Scenic 5K through vineyards and farm at Rocklands Farm Winery with chip timing, post run wine options, live music, and awards for overall and age group finishers.
A Harford County Running Club Sunday run in Havre de Grace with a self timed, stroller friendly 4 mile road course and optional extra mileage around a hay field.
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 in Little Orleans, MD featuring a 50K and 25K on out and back courses with multiple aid stations and official cutoff times.
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.
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.
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.
50K and 20K trail races on largely single track loops through Rosaryville State Park near Upper Marlboro, MD, organized by Annapolis Striders.
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 November event in Brunswick MD with a full marathon, half marathon, and a Veterans Challenge 5K that features towpath running, river crossings, and historic town sections.