Trail Running calendar near Highfield-Cascade 2026-2027

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.

Experience the beauty of Western Maryland at Rocky Gap State Park with 25K and 50K trail races. Run solo or join a relay team to navigate three distinct loops featuring scenic lake views and ridge traverses.

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.

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.

Evenstar Ultras is a timed trail event at Shenandoah River State Park with 3, 6, 12 and 24 hour options on a 3.48 mile loop. Frequent returns to the main aid station reduce the need to carry heavy gear.

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-funded *5.25 mile* trail race at Gunpowder State Park on October 18, 2026, featuring a steep early climb, downhill sections, and single-track trail. No registration fee and race day registration is available.

A trail event in Patapsco Valley State Park offering in-person and virtual 50k and 25k options, finishers awards including a hand-thrown mug, five aid stations, and a virtual completion window from Oct 24 to Nov 24, 2026.

A 50 mile ultra plus 50 km, half marathon, and relay teams from 2 to 8 runners through Rothrock State Forest near Boalsburg, PA on October 24, 2026, with staffed aid stations and support vehicle options for ultras.

A themed, untimed trail event at Camp Anderson on October 24, 2026 where runners wear flag belts and navigate zombie zones. The event features runner and zombie roles, costume encouragement, awards, and proceeds benefiting local organizatio..

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.

The 5th Annual Mackyard Ultra is an ultramarathon hosted by the Baltimore Road Runners Club at Shawan Downs in Cockeysville on October 31, 2026. Entry is $20 and the field is limited to 100 runners with pre registration on RunSignUp planned..

Trail race in Little Orleans, Maryland on November 1, 2026 offering 25K and 50K courses on mixed trail and road terrain, multiple aid stations, official cutoffs, training runs, and a series reward program.

A trail event at Brush Mountain Sportsmen’s Association in Altoona with 10K and 5K races, a 5K walk, and a half mile youth race for ages 5 to 12. Awards and a post race gathering follow the races.

An annual trail event at Gifford Pinchot State Park that raises funds for canine cancer research, featuring a 5k run and a 3.5k walk with awards for canine human teams and solo runners.