Maryland
Maryland Trail Running Calendar 2026-2027
Explore the best trail runs in Maryland for 2026-2027! Our updated list features 76 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
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 on October 18, 2026 featuring a steep opening climb, single track sections, downhill stretches, and donation based entry.
A 5K walk and run on October 18, 2026 at the Ma and Pa Trail Williams St trailhead in Bel Air, MD; registration $20 from Sept 26 to Oct 15 and finishers receive a Husky medal.
Trail event at Patapsco Valley State Park offering 50k and 25k distances with on-site and virtual options, aid stations, shirts, and distinct finishers awards.
Scenic 5K through vineyards and farm at Rocklands Farm Winery with chip timing, post run wine options, live music, and awards for overall and age group finishers.
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.
Nighttime Halloween themed trail 5K at Pemberton Historical Park in Salisbury, MD, with single track, sandy and root covered trails, costume prizes and chip timing.
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 races in Little Orleans, MD featuring a 50K and 25K on out and back courses with multiple aid stations and official cutoff times.
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.
A benefit run and walk along the Patuxent River supporting conservation, with USATF-certified 5K and 10K courses and a 3K fun walk.
An 11 mile out and back trail race in Cunningham State Park, Thurmont MD, with a single aid station at 5.5 miles and roughly 2200 feet of elevation gain.
Trail 5k and 10k at Rock Creek Regional Park supporting The Rock Creek Foundation, with chip timing, medals, shirts, a virtual option, and series points.
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.
A scenic 5K at Milburn Orchards in Elkton on November 8, 2026, across orchard and farm trails with a portion of proceeds donated to local organizations.