Maryland
Maryland Trail Running Calendar 2026-2027
Explore the best trail runs in Maryland for 2026-2027! Our updated list features 74 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
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.
Support Patuxent River wildlife conservation by participating in a 10K, 5K, or 3K walk along a flat course through scenic river banks and wildlife sanctuaries.
An 11 mile out-and-back trail race in Cunningham State Park near Thurmont MD with about 2200 ft elevation gain and an aid station at the 5.5 mile turnaround.
Scenic 5k and 10k trail races at Rock Creek Regional Park on November 7, 2026, with a virtual option and proceeds benefiting The Rock Creek Foundation.
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.
Experience the natural beauty of Rosaryville State Park at this classic single track trail race featuring 50K and 20K distances through wooded meadows and rolling hills.
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.
Free BRRC GPS 5K at Herring Run Park featuring mixed paved, field and single track terrain, two river crossings, and course variations from local high school routes.
A 5 km on the Mason-Dixon Trail in Darlington with two multi-loop challenge options and self-timed results, free registration.
Experience the beauty of Maryland trails with the Tuckahoe 25k, a scenic race through single track paths and horse trails featuring fully stocked aid stations and festive churros.
Flat out and back 5k and 10k on the C&O Canal towpath at Carderock Recreation Area on November 22 with walkers welcome and a virtual option.
Celebrate Thanksgiving with a cross country style race through scenic Catonsville. Support the local high school running program with a chip timed 5K or a 1 Mile Family Fun Run for all ages.
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.
Scenic 5k and 10k at Wheaton Regional Park with chip timing, a technical shirt and finisher medal, a virtual option, and series points.