Trail Running calendar near Winchester 2026-2027

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 miles trail ultramarathon in the Massanutten range with 22,300 feet of climbing and a 48 hours limit. The reverse MMT route uses rugged singletrack, includes two climbs of Waterfall, and requires crew support for the second half.

Experience a technical trail race with your dog at a scenic equine rehabilitation facility in Virginia. Enjoy distances from 1.25 miles to 10K followed by a finishers festival with food trucks and a biergarten.

A 12 hour trail run at Prince William Forest Park featuring a 6.5 mile figure eight loop on single track and fire road, two aid stations, and options for solo or two person relay teams.

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 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-based event at Pohick Bay Regional Park on October 4, 2026, offering in-person 5K and 10K races plus virtual options with different medal and shirt choices.

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 at Shenandoah River State Park where runners complete as many 3.48 mile loops as possible in 3, 6, 12, or 24 hour options. Supported aid, a hoodie, finisher awards, and a special 100 mile award are included.

A scenic, flat 5K and 10K at Bluemont Park in Arlington on October 17, 2026, with in-person and virtual entry options. Walkers and strollers welcome and tiered registration pricing applies.

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 weekend of obstacle racing at Massanutten Resort with 5K and 10K courses, a kids race and spectator tickets. The mountain course uses rocky trails and steep climbs and lodging and service member discounts are available.

Andy's Backyard Ultra is a last person standing ultra at Teventrails in Earlysville, VA where runners complete a 4.17 mile loop each hour. The final finisher is the runner who completes one more lap than all other entrants.

A marked trail competition in Prince William Forest Park offering a 25 km one loop and a 50 km two loop option with on course aid stations. Entry opens September 15, 2026 and the field is limited to 110 runners.

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.