Trail Running calendar near Sykesville 2026-2027

A fourth-annual trail event at Glenroy Preserve with looped 5 mile, 25K, and 50K courses featuring mixed technical terrain, multiple creek crossings, four aid stations, and post-race food and beer for 21 plus.

Experience a unique trail run through 1600 acres of former prison grounds at Laurel Hill Park. Choose between 5.4 or 10 mile distances on scenic singletrack featuring historic guard towers and open meadows.

In-person 5K and 10K races on the trails of Pohick Bay Regional Park in Lorton VA plus virtual options with medals and shirts; walkers are welcome.

District 19 in Anacostia on October 4, 2026 is a run crew led, unsanctioned road and trail event offering 5K, 19K and 19 Mile options with course markers, corral seeding, and a shirt, snack, and medal for finishers.

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.

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.

Trail races at Lums Pond State Park in Bear DE offering 24 km, 12 km, and 12 hour solo and relay formats with age graded results and on course aid.

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.

Autumn races at Laurel Hill Park on October 17, 2026 offering 5K, 10K, a half marathon and virtual options with varied entry fees.

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.

Marathon and half marathon on a flat, USATF certified C&O Canal Towpath course starting and finishing at Fletcher's Cove in Washington DC with aid stations and finisher medals.

Fall Run for the Wounded on Oct 18, 2026 features 5K, 10K and a half marathon through Prince William Forest Park with in-person and virtual options.

Experience the scenic singletrack trails of Lake Fairfax Park with 5 mile and 10 mile race options. Enjoy a community atmosphere with post race breakfast and a dedicated program for children.

A donation supported 5.25 miles trail race at Gunpowder State Park with a steep opening climb, single track sections, and on site race day registration.

Trail ultramarathon in Patapsco Valley State Park offering 50k and 25k options, in-person and virtual, with aid stations, event shirt, and finisher awards.

A marked trail competition in Prince William Forest Park offering a 25 km one loop and a 50 km two loop option with on course aid stations. Entry opens September 15, 2026 and the field is limited to 110 runners.

Trail run at Conway Robinson State Forest in Gainesville, VA offering 5 km and 10 km distances plus virtual options with medals and shirts.

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.

5th Annual Mackyard Ultra is a race by the Baltimore Road Runners Club on October 31 at Shawan Downs in Cockeysville, MD with a $20 entry fee and a 100 runner limit.

Trail race in Little Orleans MD on November 1, 2026 offering 50K and 25K courses through Green Ridge State Forest with multiple aid stations.