Trail Running calendar near Winchester 2026-2027

A campus 5K run/walk on September 19, 2026 in Middletown, VA, with online registration, set fees, age group awards, and proceeds supporting a scholarship and employee wellness initiatives.

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.

SPEAR 50K is a 50 kilometer trail race on September 19, 2026 at Sherando Park in Stephens City, Virginia. It is part of the Sherando Park Endurance Athletic Runners summer trail series and lists details and registration on RunSignUp and Fac..

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.

Trail and bike events at Sherando Park on September 26, 2026 offering a 4 mile trail race, a one mile untimed fun run, and a 5.3 mile mountain bike time trial. Proceeds benefit the I'm Just Me Movement.

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 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..

Adventure Trail Run in Prince William Forest Park on October 3, 2026 offers a 30 km option plus a 12 hour timed event and a 2 person relay. The course is a 6.5 mile figure eight loop on trails with about 650 feet elevation gain per loop.

A trail 5K at Claude Moore Park in Sterling, VA on October 3, 2026, featuring forest and leaf-covered paths. The event is the fourth race in the Run Your PRCS Parks series and includes in-person and multiple virtual entry options.

A community trail festival in Shippensburg offering a half marathon, 5k, hike, 25 mile bike ride and a free 1 mile fun run for kids, with proceeds supporting the Cumberland Valley Rails to Trails Council.

Join this annual community trail run through the wooded trail network of Potomac Shores. Residents and guests can choose between 5K and 10K courses for a free morning of outdoor activity in Dumfries.

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.

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.