Trail Running calendar near Little Orleans 2025-2026

Run the Rock Leesburg is a unique trail 5K inside an active rock quarry at Luck Stone, with gravel terrain and scenic views. Family fun, finisher medals and proceeds support the Reeves Community Center Foundation.

Lace up for the Bluemont Station Brewery and Winery 5k on April 26, 2026, a three lap cross country run around scenic winery grounds with some rolling hills. Walkers are welcome and a virtual option lets you join from anywhere.

Run scenic trails at Agricultural History Farm Park for the Farm Park Challenge. Choose marathon, 25K or 3 hour, 6 hour or 10 hour lap challenges where each lap must be under an hour. Volunteers get the same swag as finishers.

Challenge yourself on the Massanutten Mountain Trails 100 Mile Run, a rugged trail ultramarathon in Virginia with more than 18,000 feet of climbing. Expect rocky singletrack, well stocked aid stations, and a 36 hour cutoff.

Run the Dash Through the Dirt May 16, 2026 at Carderock on the scenic C&O Canal towpath in Potomac MD. Choose 5k, 10k or half marathon on light gravel with chip timing, tech shirt and finisher coin. Proceeds benefit EOD Warrior Foundation.

Tackle the legendary Old Dominion 100, a 100 mile cross country endurance run near Fort Valley, Virginia with a history dating to 1979. Expect rugged mixed terrain, volunteer support and a silver buckle for finishes under 24 hour.

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..

Ironstone 100K is a rugged 100 km trail ultramarathon through the Allegheny wilds on July 11 and 12, 2026. Expect remote terrain, minimal aid stations and no pacers for a true self reliant test of endurance.

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..