Trail Running calendar near Little Orleans 2026-2027

A multi-event trail day at Duman Lake County Park on October 3, 2026 featuring a marathon, 15 mile race, several 5k options including an AWD division, a novelty 0.0k, and a casual 26.2 mile group bike ride.

A trail 5K at Claude Moore Park on October 3, 2026, featuring forest and leaf-covered trails, part of the Run Your PRCS Parks timed series, with in-person and multiple virtual entry options.

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.

A technical trail 10K at Black Hill Regional Park with rocky and rooty terrain. The race is part of a low key series, free for club members and available to non members for a fee with on site bib and chip pickup.

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.

Timed trail event on a 3.48-mile loop in Shenandoah River State Park with 3-, 6-, 12-, and 24-hour options, on-course aid, awards, and required lighting for night segments.

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 roughly 2 mile untimed loop at Camp Anderson on October 24, 2026 where runners, walkers and costumed zombies navigate Zombie Zones and flag belts. Proceeds benefit Tyrone Snyder Public Library and Camp Anderson.

Trail races at Conway Robinson State Forest on October 25, 2026, offering 5K, 10K and several virtual options with medal and shirt choices; walkers are welcome.

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.

A Halloween nighttime 5-mile out-and-back on the Ghosttown Trail in Vintondale, PA, held October 31, 2026. The closed-course event requires personal lighting, uses chip timing, includes one water stop, awards by age groups, and has a 1 hour..

Fire on the Mountain on November 1, 2026 in Green Ridge State Forest offers two trail distances, about 32.8 miles and 16.3 miles, on red and green trails with technical sections, several aid stations, and a midpoint oasis.

Experience a mix of twisty singletrack and open farm field running in Germantown. This late autumn trail event offers three distances and a festive post race atmosphere at the historic Button Farm.

Experience a 50 mile trail race through the scenic Seneca Greenway and Muddy Branch trails in Maryland. This event features forested single track terrain and small stream crossings for dedicated distance runners.

Run Through the Grapevine is an 8K cross country race at Linganore Winery in Mount Airy, Maryland on November 8, 2026. The course runs through vineyard rows and adjacent hop yards, and all finishers receive one free winery tasting.

Trail races at Hemlock Overlook in Clifton, VA offer two loop options, 5.2 miles or 9.5 miles. The course follows hiking trails, dirt roads and fields along Bull Run and includes designated spectator areas and park facilities.

A pre-Thanksgiving 3K and 6K at Barrel Oak Winery and Brewery in Delaplane, VA on November 15, 2026. In-person runs and virtual entry options are available; walkers and leashed pets are allowed.

A 48 hour out and back ultramarathon inside Sideling Hill Tunnel covering just under 160 miles. A Toll Ticket system limits exits and shifts emphasis to psychological endurance and strategic planning.