Trail Running Calendar Maryland 2026-2027

A five-mile towpath race in Williamsport, MD, held as the 45th annual Gary Brown Memorial event. Entries include standard and student fees, a guaranteed T-shirt deadline, chip timing with instant results, podium awards, and designated parki..

Trail Trotters 5k & Fun Run is a community trail event at Promise Landing Farm in Upper Marlboro on June 7, 2026. The event features a 5k and a fun run; adult registration includes a T shirt and concessions with live music.

A chip timed 5k at Corteau Vineyards in Mechanicsville, Maryland on June 13, 2026, featuring vineyard scenery, a t-shirt, collapsible wine glass, finisher medal that doubles as a wine stopper, and an on-site wine pour.

A self-timed 4 miles run in Bel Air as part of the Harford County Running Club Dog Days of Summer Series. The course mixes trail and road, is not stroller friendly, and parking is at Prospect Mill Park.

A Juneteenth trail event in Germantown on June 19, 2026 offering 6K and 12K distances plus virtual options, with a hilly course around Button Farm and the Schaeffer Farm Trails and welcome to walkers.

A rugged out-and-back trail race near Frederick, MD, offering a 50K and a 25K Half Cat on rocky, shaded singletrack with stream crossings, three aid stations, and mandatory on-course hydration.

A free night training run in Salisbury, MD offering six hours of repeated 5K loops on marked trails. Space is limited to 50 runners and participants must provide their own hydration and fuel.

Kick off the Blue Crab Bolt series at Seneca Creek State Park with scenic 5K and 10K trail runs featuring lake views and singletrack paths. Enjoy professional race support, post-run breakfast burritos, and a festive atmosphere.

MCRRC Cross Country on the Farm Trail 5K is a trail race at Agricultural History Farm Park in Derwood MD. Non member registration is available for a $20 fee and the event is part of the club's low key race series.

A themed Forrest Gump fun run at Lakeside Loop in New Town Village, Owings Mills, offering a full 4.4-mile loop or a 1-mile out-and-back option. The event is free and participants are encouraged to wear the red hat, yellow top and red short..

A trail-based running event at Needwood Lake Circle in Maryland on July 11, 2026 offering 5 km, 10 km and virtual entries with medal and shirt options.

A trail race at Gunpowder State Park listed as 7 miles with a route that crosses county lines, features rolling hills, water crossings and occasional mud. Registration is free and donations are accepted on race day.

A timed six-hour endurance event at Quiet Waters Park in Annapolis with solo and three-person relay formats. The course is about 4.25 miles per loop, with aid stations on the route and awards by overall and age-group distance.

Experience the twisty single track and scenic farm fields of Germantown at this trail running event. Participants can choose between two distances while supporting local non profits in Montgomery County.

Trail races at Bohemia Manor Farm Winery featuring *5K* and *8K* courses through vineyards, riverfront and wooded trails, chip timing with live results, finisher wine glass and an on-site after party with music and food.

Run through the wooded singletrack trails and streams of Little Bennett Regional Park in Maryland. Enjoy a community atmosphere with professional timing, post race breakfast burritos, and distances for different experience levels.

An 8K cross-country race at Anne Arundel Community College on August 2, 2026, part of the Annapolis Striders Championship and Maryland/DC RRCA Grand Prix Series, with pre-registration fees and race day registration available.

A wooded trail race at Gunpowder State Park on August 9 with mostly single track loops of about 4 miles. Participants can run one loop for 4 miles or two loops for 8 miles.

A trail race in Elkridge, MD on Aug 15, 2026 offering 25K and 50K options on rolling single track with river crossings. Aid stations provide water and real food and the finish area includes food, beer, and shelter.

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.