Trail Running Calendar Maryland 2026-2027

Trail races at Bohemia Manor Farm in Chesapeake City feature 5K and 8K courses through vineyards, wooded trails and along the river, with chip timing, age group awards, finisher wine for ages 21 plus and an on-site after party with music an..

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.

Part of the Harford County Running Club Dog Days of Summer Series, Rigbie Farm 5k is a free, self timed grass and trail loop near Darlington, MD. Parking is at Rigbie Farm and non members may take part in three free runs.

Trail races on mostly single-track loops in Gunpowder Falls State Park, offering one or two 4-mile loops (4 or 8 miles); the course avoids the overgrown north river trail this year.

Trail race in Elkridge, MD offering 25K and 50K on rolling single track with river crossings, aid stations serving real food, and post-race food and beer.

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 on the NCR Trail in Cockeysville, MD, held August 19 as part of the Baltimore Road Runners Club 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..

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.

Family friendly mud run at Budds Creek Motocross Park on August 29, 2026 featuring a 5K course with obstacles, mud pits, slides and a festival style after party.

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.

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.

Carderock Charge offers 5K, 10K and a half marathon on the flat C&O Canal Towpath in Potomac, MD on September 6, 2026.

A 24 hour event in Salisbury where individuals and teams of four run repeated 5K loops each hour, earning points for finishes and extra points during the overnight window.

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 5K on the Ma & Pa Trail in Baltimore on September 26, 2026 with in-person and virtual options supporting Cancer Warriors Inc.

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.