Trail Running calendar near Montgomery County 2026-2027

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.

An annual 5K hosted by Cancer Warriors Inc. in Baltimore on September 26, 2026, featuring an out-and-back course on the Ma & Pa Trail, a virtual 5K window in early September, and proceeds supporting cancer research.

The Bull Run Reunion Run will take place in Parkton on Saturday 26 September 2026. You can run 3 miles.

Experience a supported long distance run on the hardpacked dirt and gravel of the Torrey C. Brown Trail. This twenty mile event serves as an ideal training opportunity for those preparing for a fall marathon.

A 10 miles trail race in Holtwood, PA, over rocky, hilly trails with stream crossings and scenic overlooks. Chip timed, with aid stations, a strict 2.5 hour cutoff to mile 7, and one way bus transport to the campground start.

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.

Trail canicross races at Caledon State Park offer two distances, allow leashed dogs, and provide a reusable speedCup; entry fees support Friends of Caledon State Park.

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..

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.

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.

Trail races at Glenroy Preserve on October 4, 2026 offering 5 mile, 25K, and 50K loops with mixed and technical terrain, multiple creek crossings, four aid stations, chip timing, and post-race refreshments.

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.

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.