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!
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 scenic chip-timed 5K on the 300+ acre Running Hare Vineyard in Prince Frederick, MD, featuring a complimentary drink for those 21 and over, live music, finisher medals, apparel options, and proceeds supporting Habitat for Humanity.
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 community event at Assateague State Park offering a 2 mile walk or 5K run to support the Macky & Pam Stansell House of Coastal Hospice.
A donation supported 5.25 miles trail race at Gunpowder State Park with a steep opening climb, single track sections, and on site race day registration.
Trail ultramarathon in Patapsco Valley State Park offering 50k and 25k options, in-person and virtual, with aid stations, event shirt, and finisher awards.
Scenic 5K through vineyard and farm at Rocklands Farm Winery with chip timing, age group awards, and a post-race wine tasting with live music. Walkers and children are welcome and a one hour course time limit applies.
5th Annual Mackyard Ultra is a race by the Baltimore Road Runners Club on October 31 at Shawan Downs in Cockeysville, MD with a $20 entry fee and a 100 runner limit.
November 2026
Trail race in Little Orleans MD on November 1, 2026 offering 50K and 25K courses through Green Ridge State Forest with multiple aid stations.
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.
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.
Looped 50K and 20K trail races at Rosaryville State Park near Upper Marlboro MD, single track woods, two aid stations, drop bag support and military awards.
A free 5K cross country at Herring Run Park on November 15 featuring mixed surfaces, two river crossings, wooded trails, and donations accepted for local scholarships and park support.
A 25K trail race in Queen Anne, MD on November 21, 2026 featuring single-track and horse trails, three aid stations, and awards for top finishers.
In-person 5 km and 10 km races on the flat Chesapeake and Ohio Canal Towpath at Carderock Park in Potomac, MD, with virtual entry options on November 22, 2026.