Trail Running calendar near Winchester 2026-2027

A Juneteenth trail event in Germantown on June 19, 2026 offering 6K and 12K distances plus virtual options, with a hilly course around Button Farm and the Schaeffer Farm Trails and welcome to walkers.

A summer cross-country series with four races, three confirmed at local high schools. Online pre-registration is free and a $5 cash fee is collected on race day.

A 40 mile trail ultrarun on June 20, 2026, centered at Canaan Valley State Park in Davis, West Virginia. The route crosses the Monongahela National Forest and includes Roaring Plains and Dolly Sods Wilderness.

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..

A 5 km and 10 km event along the Chesapeake and Ohio Canal path in Georgetown, Washington, DC on June 20, 2026. Walkers are welcome and registration fees vary by date with separate pricing for each distance.

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.

A themed Forrest Gump fun run at Lakeside Loop in New Town Village, Owings Mills, offering a full 4.4-mile loop or a 1-mile out-and-back option. The event is free and participants are encouraged to wear the red hat, yellow top and red short..

A trail-based running event at Needwood Lake Circle in Maryland on July 11, 2026 offering 5 km, 10 km and virtual entries with medal and shirt options.

A 5K and 10K event at Nottoway Park in Vienna, VA on July 11, 2026, with multiple virtual options and tiered entry fees.

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.

Christmas in July 5k & Half in Georgetown, Washington DC on July 25, 2026 features races along the Chesapeake and Ohio Canal path with 5K, half marathon and virtual options; walkers are welcome.

Trail races on the Lost Turkey Trail near Blue Knob State Park in Pennsylvania offer a 50K point to point, a 13.1 mile loop and a 10K(ish) option on single track and double track terrain.

Locust Shade 5k and 10k on July 25, 2026 uses shaded scenic trails at Locust Shade Park in Triangle VA. Walkers are welcome and virtual entries are available with medal and shirt options.