Trail Running calendar near Keswick 2025-2026

The Mountain & Vine Vineyard 9k is a scenic and challenging race held at Mountain & Vine Vineyards in Faber, Virginia. The event offers three distances: 3k, 6k, and 9k, with the 9k consisting of three laps around a hilly course featuring some tough summits and rewarding views. Participants receive a..

The Barrel Oak 6k is a scenic and challenging cross-country race held at Barrel Oak Winery in Delaplane, Virginia. The course features two laps of a 3k route that winds through vineyards, including gravel dirt roads and some hills, offering varied terrain and elevation. Walkers and leashed pets are..

The Massanutten Mountain Trails (MMT) 100 Mile Run is a challenging ultramarathon held in the Massanutten Mountains within Virginia’s Shenandoah Valley. Starting and finishing at Caroline Furnace Lutheran Camp in Fort Valley, VA, the rugged course features rocky trails and steep climbs totaling over..

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 unique event tests runners' versatility across multiple ter..

The OSS/CIA 50 Mile Night Run is a challenging ultramarathon held in Prince William Forest Park, Virginia, a historic site once used to train World War II OSS spies. The race features a 25+ mile loop primarily on single-track trails, fire roads, and several bridge and road crossings, which runners c..