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!
September 2026
A 24 hour festival of hourly 5K races at Pemberton Park in Salisbury, MD, where individuals and four person teams earn points per 5K with nightly bonuses.
A chip-timed 5K run/walk at Running Hare Vineyard on September 19, featuring a race shirt (if registered by Aug 31), a drink ticket, finisher medal, and awards by age group.
Open 6k at Terrapin Nature Park in Stevensville, MD on September 19, 2026; open to all, $25 entry, flat sandy gravel course with bay views.
Annual 5K trail run and family fun run at Terrapin Nature Trail on Maryland's Eastern Shore with a separate 1 mile kids run.
An in-person event on September 26, 2026 in Brunswick, MD featuring a trail-based 5K and timed 3-hour and 6-hour challenges on a 5 mile loop. Proceeds support Brunswick High School Track and Field equipment.
Run On The Rocks in Point Of Rocks, MD on September 26, 2026 features 10 mile, half marathon and 20 mile events. The race is chip timed and includes participant shirts, finisher medals and age group awards.
Cancer Warrior 5K on September 26, 2026 raises funds for cancer research with an after party hosted by Independent Brewing and an early registration discount.
A 3 mile Reunion Run at Hereford High School as part of the Bull Run Cross Country invitational. The race is open to all ages and carries a $10 registration fee, with registration listed from August 24 to September 26.
A 20 mile supported trail run on the Torrey C. Brown NCR Trail in Freeland, Maryland, offered in both in-person and virtual formats.
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 2 mile walk and 5K run at Assateague State Park on October 17, 2026 benefiting the Macky & Pam Stansell House; includes a shirt and medals.
A 5.25 mile trail race at Gunpowder State Park with a steep opening climb, single-track sections, a fast finish, and race day donation based registration.
Trail 50k and 25k races at Patapsco Valley State Park with in-person and virtual options, aid stations, event swag, and distinct finishers 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.