Trail Running calendar near Gordonsville 2025-2026

Run through vineyards at Barrel Oak Winery on 3k and 6k cross country courses with gravel and rolling hills. Enjoy a finisher medal, tech shirt and a glass of wine while supporting Semper Fi and America's Fund, virtual option available.

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.

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 Motion for Justice 5k in Rocketts Landing along the scenic Virginia Capital Trail with James River views. Enjoy a finisher medal and technical shirt or go virtual if you cannot attend in person.

The Old Dominion 100 Endurance Run, held in Fort Valley, Virginia, is a challenging 100-mile race featuring a diverse course that includes pavement, gravel roads, single-track trails, ATV trails, logging roads, rocks, streams, and mud. This..

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.

Night Train is an evening trail run along the scenic High Bridge Trail in Farmville, VA, offering distances from 5K to 50K plus a family 5K option. Start and finish at Camp Paradise and enjoy a memorable finish across the bridge.

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.

Take on the Odyssey Trail Running Rampage at Douthat State Park on September 12, 2026, with four loop distances from six miles to 50K on rugged trails with steep climbs. Expect chip timing, a performance shirt, finisher pint mug and post ra..

Explore scenic new hiking trails at Pocahontas State Park with options of a half marathon or 10k, both starting and finishing on the park's grass field. Pro chip timing and live results add a competitive edge to this fall trail run.

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..