Maryland
Maryland Trail Running Calendar 2026-2027
Explore the best trail runs in Maryland for 2026-2027! Our updated list features 67 exciting trail runs across the region. Find your next trail run in Maryland below and join the trail community at these great events!
August 2026
Muddy Dash Mechanicsville on Aug 29, 2026 is a family-friendly 5K mud run with obstacles, mud pits, a pre-party and an after-party at Budds Creek Motocross Park.
A 3.8 mile running event at Pen Mar Park that climbs about 1.8 miles to High Rock Overlook and returns to the park. Registered finishers receive an official High Rock Mountain t-shirt and there are early and race day fee options.
A self-timed loop-trail event in Havre de Grace on 08/30/2026 with a listed distance of 3 miles. Runners have 90 minutes to complete as many loops as they like; parking is at Steppingstone Farm Museum.
September 2026
A 10K road race and a 5K road/trail combo at the Shrine of St Anthony in Clarksville, MD on Sept. 5, 2026. Both USATF certified with chip timing, guaranteed shirts for early registrants, music and family activities.
Fast, flat 5K, 10K and half marathon at Carderock Recreation Area on September 6, 2026, with virtual options and walkers welcome.
A 24-hour series of hourly 5Ks at Pemberton Park in Salisbury, MD, where solo runners and four-person teams earn points for each completed lap.
Sip and Stride 5K is a chip timed run and walk through Running Hare Vineyard in Prince Frederick, Maryland on September 19, 2026. Entry includes a shirt option, a drink ticket for 21 plus, and a finisher medal.
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 community charity race in Gaithersburg on October 3, 2026, featuring cross-country 10K and 5K, a paved 1-mile accessible fun run, and a kids Trike-A-Thon. Proceeds support Comfort Cases and Covenant Life School and include a post-race backpack-pack..
A chip timed 5K at Running Hare Vineyard on October 11, 2026 with a scenic course, post race music, food vendors, and a complimentary drink for participants 21 and over.
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.