Maryland
Maryland Trail Running Calendar 2026-2027
Explore the best trail runs in Maryland for 2026-2027! Our updated list features 65 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
Trail races in Elkridge, MD offering 25K and 50K on rolling single track with river crossings, aid stations, and an onsite after party.
A 7K trail race at The Woodstock Equestrian Center in Dickerson, Maryland, presented as part of MCRRC's low key series for members. Non member registration has a $20 fee and runs from February 10, 2026 to August 16, 2026.
An evening 4 mile out and back run on the NCR Trail at Paper Mill in Cockeysville, part of the BRRC Grand Prix Series on August 19, 2026.
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 and music.
A self-timed 5 miles on a packed rail trail in Darlington, Maryland, held as part of the Harford County Running Club Dog Days of Summer Series. The course is stroller friendly with parking at Fisherman's Log and free registration.
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.
Races on September 6, 2026 at Carderock Recreation Area in Potomac, MD offering 5K, 10K and Half Marathon courses described as fast and flat with virtual options.
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.
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.
A community 5K in Baltimore on September 26, 2026 with in person and virtual options, organized by Cancer Warriors Inc. to raise funds for cancer research.
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.
Experience a supported long distance run on the hardpacked dirt and gravel of the Torrey C. Brown Trail. This twenty mile event serves as an ideal training opportunity for those preparing for a fall marathon.
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 adult.
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.