Trail Running Calendar Maryland 2026-2027

A 7K trail race at the Woodstock Equestrian Center with a hilly course that circles fields and runs through wooded single track, presented as a 1969 throwback with 60s music and period attire encouraged.

GPS Too Hot to Trot is a four mile out and back race on the NCR Trail starting at the Paper Mill parking lot in Cockeysville, MD on August 19, presented as part of the Grand Prix Series.

A memorial 5K trail run at Genesee Valley Outdoor Learning Center in Parkton, MD, with a 5K, 1-mile walk, kids dash, team entries, and an In Spirit donation option. Proceeds support a scholarship fund and a post-race festival offers food an..

Muddy Dash Maryland is a mud obstacle event at Budds Creek Motocross Park on August 29, 2026 offering Value and VIP registrations, packet pickup the day before, free spectator admission, and a program donating registrations to local communi..

An out-and-back 3.8 mile run at Pen Mar Park with about 1.8 miles of ascent to High Rock Overlook. Held August 30, 2026, with registration deadlines and a higher fee on race day.

A 24-hour event at Pemberton Park where individuals and four-person teams run repeated 5K loops, earning points per finish and for placing, with bonus points for late-night miles and a big bonus for completing all 24.

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.

Cancer Warrior 5K on September 26, 2026 is a community running event supporting cancer research. The day includes an after party at Independent Brewing, raffle items from local sponsors, and a ghost runner option for remote participants.

An annual community 5K run and walk at Agricultural History Farm Park in Derwood, Maryland on September 27, 2026, organized by MD District 15 Democratic Caucus. Offers adult and youth entries plus a free youth option with an accompanying ad..

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.

A technical trail 10K at Black Hill Regional Park with rocky and rooty terrain. The race is part of a low key series, free for club members and available to non members for a fee with on site bib and chip pickup.

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.

GPS Big Gunpowder Trail is a 5.25 mile trail race at Gunpowder State Park in Kingsville on October 18, 2026. The course includes a steep start, downhill and single track sections, and entry is donation based with race day registration avail..

A trail event at Patapsco Valley State Park with in person and virtual 50k and 25k options, event swag, aid stations, and a finishers mug or medal.

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.

Fire on the Mountain on November 1, 2026 in Green Ridge State Forest offers two trail distances, about 32.8 miles and 16.3 miles, on red and green trails with technical sections, several aid stations, and a midpoint oasis.

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.