Trail Running calendar near Woodstock 2026-2027

A Juneteenth trail event in Germantown, MD offering 6K and 12K routes around Button Farm and the Schaeffer Farm Trails. The course is hilly and scenic, walkers are welcome, and virtual participation options are available.

Highlands Sky is a 40 mile trail run in Davis, West Virginia on June 20, 2026, centered at Canaan Valley Resort State Park. The route goes through Monongahela National Forest and Dolly Sods with meadows, bogs, and rocky plains.

A rugged out-and-back trail event in Cunningham Falls and Gambrill State Parks on June 20, 2026 offering a 50K and a 25K Half Cat with three aid stations, strict crew and hydration rules, and a recently rerouted section that lengthens the c..

Scenic 5K and 10K runs along the Chesapeake & Ohio Canal path in Georgetown, Washington, DC, on June 20, 2026. Walkers are welcome and registration fees vary by date.

A trail race in Canaan Valley State Park on June 27, 2026 with one loop of 5.9 miles or two loops for 11.8 miles on the Promised Land Trail, about 350 feet elevation gain per loop. Field is limited to 200 runners.

Trail races at Seneca Creek State Park on June 27 2026 feature 5K and 10K courses through lakeside singletrack and streams, with aid stations, park parking, post race food, and age category awards.

A 12 hour trail race on a five mile single track loop in Berkeley Springs WV with technical terrain and about 750 feet of elevation gain per loop. Full aid at start and finish, awards and a 50 Mile Club recognition for 10 loops.

A 5K trail race at Agricultural History Farm Park in Derwood, Maryland. MCRRC members run free with a 2026 bib and chip while non members pay a set fee and can register online through race start.

A free 5K fun run on July 4, 2026 organized by Great Falls TrailBlazers. The loop course goes through the woods, meets at the Great Falls Library, is open to all ages and is pet friendly.

Rock the Heat offers scenic 5 km and 10 km races on July 11, 2026, through Rock Creek Regional Park with multiple virtual options and a medal donation initiative for Medals4Mettle.

A 5K and 10K held at Nottoway Park in Vienna on July 11, 2026, with in-person and virtual entry options; published registration fees vary by entry date and include mandatory charges.

A lakeside trail race at Boar's Head Resort in Charlottesville on July 11, 2026, featuring a 5.2 mile loop with about 745 feet of elevation change. The race is open to runners and walkers and is part of the Summer Trail Running Series.

A roughly 50 km trail ultramarathon on the southern Massanutten range with about 5,700 feet of elevation gain, six aid stations, and a post run gathering at the Route 211 commuter parking lot. Entry is limited to 75 runners.

Experience the West Side Quarry trail race along the Rappahannock River in Fredericksburg. This 10k course features a steady climb and rolling hills with 426 feet of elevation gain for a dynamic running experience.

A vineyard run in Purcellville on July 25, 2026 offering 5k and 10k routes plus virtual entries with medal and shirt options. Registration fees vary by distance and registration date.

Trail running at Button Farm in Germantown, MD over twisty single track with stream crossings, log ramps, and farm fields. Options include a 5K and an about 10K course with aid stations, post race food, and optional medals.

A 5K and half marathon run along the Chesapeake & Ohio Canal path in Georgetown Washington DC on July 25, 2026. Walkers are welcome and virtual entries are available with medal and shirt options.

A July trail event at Locust Shade Park in Triangle, VA offering 5K and 10K distances plus multiple virtual options. The courses run on shaded, scenic trails and walkers are welcome.

Run through the wooded singletrack trails and streams of Little Bennett Regional Park in Maryland. Enjoy a community atmosphere with professional timing, post race breakfast burritos, and distances for different experience levels.

A summer trail event in Crozet, VA listed as a 30 Miler with about 29.0 miles and 7,610 feet of climbing. The steep gravel out-and-back laps include limited aid, shuttle parking, and rugged summer conditions.