Trail Running calendar near Winchester 2026-2027

The Johnnycake Jolt Series will take place in Windsor Mill on Wednesday 13 May 2026. You can run between 10 and 40 kilometers.

Run 100 mile through the rocky Massanutten Mountains in Fort Valley, Virginia, tackling rugged climbs and trails. With a 36 hour cutoff and volunteer staffed aid stations, this classic ultramarathon tests endurance and grit.

Run scenic out and back courses along the C&O Canal towpath in Potomac on May 16, 2026, with 5k, 10k and half marathon distances. Enjoy chip timing, a tech shirt and finisher coin, support the EOD Warrior Foundation, or take part virtually.

The Johnnycake Jolt Series will take place in Windsor Mill on Wednesday 20 May 2026. You can run between 10 and 40 kilometers.

Join the Night Raider at the Winery at Bull Run on May 22, 2026 for a festive evening 5k or 10k through scenic Manassas Battlefield trails. Enjoy chip timed results, a finisher medal, a technical shirt and a complimentary glass of wine.

Enjoy a scenic 5K on trails across a 100 acre organic farm by the Cacapon River in Wardensville. This family friendly fundraiser benefits local volunteer fire and rescue and the Youth Giving Committee, with food and leashed dogs welcome.

The Johnnycake Jolt Series will take place in Windsor Mill on Wednesday 27 May 2026. You can run between 10 and 40 kilometers.

Tackle 100 miles through the Massanutten Mountains and Shenandoah Valley from Fort Valley, Virginia. This scenic loop blends trails and road, climbs about 14,000 feet and serves as a true endurance test with a 24 hour silver buckle cutoff.

Run a flat, fast five mile out and back along the shaded C&O Canal Towpath in Williamsport, MD on June 6, 2026. Enjoy chip timing, tech shirt options and age group awards in a friendly community race.

Tackle the OSS/CIA 50 Mile Night Run in Prince William Forest Park with 50, 25 or 10 mile options under the stars. Enjoy single track trails, stocked aid stations and a scenic loop run twice for the 50 mile.

Run the Highlands Sky 40M, a 40 mile trail ultra through Canaan Valley and the Monongahela National Forest on the Saturday before Father's Day. Rugged plateaus, rocky plains, bogs and mountain meadows make for a scenic but demanding early s..

Run a scenic single 5.9 mile loop or a double 11.8 mile loop on the Promised Land Trail in Canaan Valley State Park near Davis WV. All finishers get a medal and McClumsy shirt plus post race snacks and a beer for 21 and older.

Run scenic single track trails at the Blue Crab Bolt Trail Run at Seneca Creek State Park on June 27, 2026. Choose a 5K or 10K and enjoy woods, lake views and streams as the kick off to the Blue Crab Bolt series.

Get muddy and fast at MCRRC XC on the Farm, a fun 5k cross country at Agricultural History Farm Park in Derwood on June 28, 2026. Open to all ages with affordable registration and a relaxed club atmosphere.

Run through rolling vines at 868 Estate Vineyards in Hillsboro with a scenic but hilly 5k or 10k course that tests and rewards. Finishers get a medal, tech shirt and a glass of vineyard wine, and a virtual option is available.

Run scenic, moderately technical trails at Schaeffer Farms in Germantown, starting and finishing at the Button Farm Living History Center. Choose a 5K or 10K for a rooty, stream crossing adventure while supporting local charities.

Run the scenic Third Winchester Battlefield on Aug 8, 2026 with 5k, 10k or half marathon options on mostly gravel trail. Chip timed event with finisher medal, tech shirt and virtual option, supporting Operation Enduring Warrior.

Run rugged single track and river crossings at MD Heat Trail Race in Patapsco Pickall, Elkridge MD. Choose 25K or 50K and expect big climbs, technical rock sections, helpful aid stations and a finish with food and beer.

Enjoy a scenic trail 5k or 10k through Leopold's Preserve in Broad Run, Virginia on Aug 23, 2026, with chip timing, medals and a tech shirt. Walkers and virtual participants are welcome and races earn points toward year long series.

Hit the forest trails at Dirt Farm Brewing on August 29, 2026 for the Inferno 5k and 10k. Tackle a scenic, technical loop, earn a finisher medal and a Dri FIT shirt, and toast with a glass of Dirt Farm beer. Virtual option available.