Trail Running calendar near Winchester 2026-2027

A trail event at Codorus State Park offering a 40-mile ultra, 40-mile team relay, and a 25K around a 5.72-mile looped course, with stocked aid station fare, camping nearby, year-by-year course direction, and awards for top finishers.

The Final Countdown Tribute at Amani Brewing in Martinsburg WV uses a 1.33 mile loop where allowed lap time shortens each circuit, eliminating runners until one remains.

Woodstock Warrior on September 19, 2026 is a multi-distance trail event at Seven Bends State Park near Woodstock, VA. The race uses a roughly 10 mile mixed-terrain loop with options up to 100 miles and a Last Man Standing Ruck.

A trail running event at Pine Grove Furnace State Park on September 19, 2026, offering a 50K, 20 Miler, and Half Marathon through northern Michaux State Forest with multiple aid stations, drop bag and crew options, and race day registration..

A multi-surface 5K run and walk on the Laurel Ridge Community College Middletown campus; family friendly and open to walkers. A portion of proceeds will support the Recovery Connection Scholarship and registration costs $30.

Trail races on Cedar Mountain include canicross, a dog friendly 5k, a trail run without dogs, and a virtual option, with awards for top finishers and a traditional hunt breakfast.

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.

Trails 4 Miles at Sherando Park on September 26, 2026 features a mixed-surface four-mile trail race, an untimed one-mile out-and-back on a paved path, and a new 5.3 mile mountain bike time trial, with proceeds to the I’m Just Me Movement.

A 33.3 mile single loop trail run in the George Washington National Forest featuring a climb of Big Schloss with 360 degree views and three aid stations. Entry is limited to 60 runners and opens August 3, 2026.

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 ad..

Experience the full reservoir trail system on this thirteen mile course in Fredericksburg. Runners navigate flowing singletrack and five distinct climbs totaling over nine hundred feet of elevation gain through scenic wooded terrain.

A 110-mile trail ultramarathon in the Massanutten range with about 22,300 feet of elevation gain, a 48-hour limit, required second-half crew support, and multiple staffed and unattended aid stations.

A canicross and trail event on October 3, 2026 in Gordonsville, VA offering competitive 10K and 5K races, a 1.25 mile sprint, a casual dog friendly 5K, and a virtual 5K, with technical trails, three water stations, and a Finisher's Festival..

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 bac..

An endurance event in Prince William Forest Park on October 3, 2026, featuring a 6.5 mile figure eight loop with a 30 km option, a 12 hour format, and a two person relay. The course is fully on trail with two aid stations and limited to 100..

A trail 5K at Claude Moore Park in Sterling, VA on October 3, 2026, featuring forest and leaf-covered trails and serving as the fourth race in the Run Your PRCS Parks timed series. In-person and several virtual entry options are available.

The 20th annual Cumberland Valley TrailFest in Shippensburg features a half marathon, 5k, hikes, a 25 mile bike ride and a 1 mile fun run on the Cumberland Valley Rail Trail. Proceeds benefit the Cumberland Valley Rails-to-Trails Council.

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.

Run or walk the trails at Pohick Bay Regional Park on October 4, 2026, with in-person 5K and 10K options plus several virtual entry choices and tiered registration fees.

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.