Trail Running calendar near Winchester 2026-2027

Tails on Trails 5K Run/Walk is the second annual 3.1 miles run, walk, and virtual event at Cacapon State Park on September 12, 2026. The wooded cross country course passes the upper lake and ends with awards and a free pup swim.

A women only trail running event at Fountainhead Regional Park on September 13, 2025 offering a half marathon and a 10k plus option. The event includes organized training runs and a course video; entry is closed.

Trails 4 Tails at Codorus State Park near Hanover, PA offers a 40 mile ultra, a 40 mile team relay, and a 25K on multi-loop trail courses with varied terrain and fully stocked aid stations.

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.

A looped trail event at Seven Bends State Park featuring roughly 10 mile loops on mixed terrain and multiple distances from 10 mile to 100 mile plus a Last Man Standing Ruck. Cutoffs, pacer rules, and awards vary by distance.

Trail races at Pine Grove Furnace State Park in Gardners, PA offering 50K, 20 mile, and half marathon courses through northern Michaux State Forest with technical single-track, notable elevation gain, staffed aid stations, and crew/drop bag..

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 12 hour trail event at Prince William Forest Park near Triangle, VA, run on a 6.5 mile figure eight loop with 650 feet of elevation gain per loop. Options include a 30 km race, a 12 hour entry, and a 2 person relay.

Fall Harvest 5k is a trail 5 km race at Claude Moore Park in Sterling, VA on October 3, 2026. The event includes an in-person 5K and several virtual entry options, and published fees include mandatory charges; promo codes are not accepted.

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.

A trail event at Pohick Bay Regional Park on October 4, 2026 offering 5 km and 10 km courses plus virtual participation options. Walkers are welcome.

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.