Maryland
Maryland Trail Running Calendar 2026-2027
Explore the best trail runs in Maryland for 2026-2027! Our updated list features 72 exciting trail runs across the region. Find your next trail run in Maryland below and join the trail community at these great events!
September 2026
A 20 mile supported trail run on the Torrey C. Brown NCR Trail in Freeland, Maryland, offered in both in-person and virtual formats.
Part of the Harford County Running Club Summer Run Series, this self-timed run and walk follows an about 5-mile route in Joppa with free registration.
October 2026
A scenic chip timed 5K at Running Hare Vineyard on October 11, 2026 with a complimentary drink for those 21 plus and post-race music and photos.
Experience a unique trail event at Milkhouse Brewery in Mount Airy featuring a 5 mile race and timed ultra challenges. Complete as many loops as possible over four or eight hours on this scenic farm course.
Experience the beauty of Western Maryland at Rocky Gap State Park with 25K and 50K trail races. Run solo or join a relay team to navigate three distinct loops featuring scenic lake views and ridge traverses.
A community trail event on October 11, 2026 at Bretton Woods Recreation Center in Darnestown, MD offering a 5K trail run and a 1 mile walk. The event raises funds and awareness for addiction prevention, education, and support.
Participate in a 10 km run through the scenic Black Hill Regional Park in Boyds. This low key event offers a straightforward racing experience for both club members and the general public in a natural park setting.
The Annual Boulder Dash at Pinesburg Quarry in Williamsport, MD on October 17, 2026 offers three distances : 5 miles, 5K and 1 mile, and the quarry will be closed during the event for safety.
A 5.25 mile trail race at Gunpowder State Park supported by donations, featuring a steep opening climb, single-track sections and race-day registration.
Trail ultraraces in Patapsco Valley State Park offering 50k and 25k distances with in-person and virtual options, aid stations, swag, and distance-specific finisher awards.
A scenic 5K at Rocklands Farm Winery with chip timing, on-course aid, awards, post race wine offerings, live music, and race day amenities.
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.
A Halloween-themed nighttime trail 5K at Pemberton Historical Park in Salisbury, MD with chip timing, costume prizes, and a family-friendly atmosphere.
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 race in Little Orleans MD on November 1 2026 offering 50K and 25K courses with aid stations, cutoff times, training runs and a participant recognition program.
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.