Trail Running calendar near Winchester 2025-2026

Run under the stars in Prince William Forest Park at the OSS/CIA 50 Mile Night Run, honoring the park's OSS legacy. Choose 50 mile or 25 mile on a scenic single track loop with aid stations and true night race atmosphere.

Experience Highlands Sky 40M, a rugged 40 mile ultramarathon through West Virginia's Monongahela National Forest and dramatic Dolly Sods. Based at Canaan Valley in mid June, expect wild mountain trails and unforgettable views.

Challenge yourself on the scenic Promised Land Trail in Canaan Valley State Park near Davis WV on June 27, 2026 with a 5.9 mile loop or an 11.8 mile double loop. All finishers get a medal and McClumsy T shirt, plus post race snacks and beer..

Take on the rugged MD Heat Trail Race in Elkridge with 25K and 50K options across rolling single track, technical rocky sections, river crossings and more than 2000 ft of vertical gain. Unwind at the post race party with craft beer, real fo..

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.

Halloween Horror 5k & 10k returns to Conway Robinson State Forest Park in Gainesville, VA, offering a forest trail race with a Halloween theme. The event features 5k and 10k distances, with the 10k being two laps of the 5k course. The loop..