Trail Running calendar near Rosaryville 2025-2026

The Molon Lave 5k is a scenic cross-country running event held at Molon Lave Winery in Warrenton, Virginia. The course features three loops around the winery property, offering a fairly flat terrain with natural vineyard surroundings. Walkers are welcome, and a virtual race option is available for r..

The Trail Demon 10k is a challenging trail running event held at Dirt Farm Brewing in Bluemont, Virginia. The course features a technical forest trail loop with tree roots, rocks, and elevation changes, offering scenic views and a demanding workout. Runners can choose between the 5k or 10k distances..

The Breeze Thru The Trees 5k is a cross-country running event held at Ruppert Nurseries, a 500-acre tree farm located in Gaithersburg, Maryland, within Montgomery County’s Agricultural Reserve. The event features a 5K run and a 1-mile fun run, offering participants a scenic course winding through a..

Run to Remember in Sykesville, MD, is a memorial running event held at Piney Run Park, featuring distances of 50K, 25K, 5.25 miles, and an 8-hour challenge. The course is a scenic 5.25-mile loop through woods and meadows, with about half the route offering lake views. Runners complete multiple loops..

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 C&O Canal 100 is a 100-mile ultramarathon held in Knoxville, Maryland, along the scenic C&O Canal towpath near the Potomac River and Appalachian Mountains. The course features one approximately 40-mile loop followed by two 30-mile loops, starting and finishing at Camp Manidokan. Runners enjoy a..

The Farm Park Challenge is a unique trail running event hosted by My Muddy Shoes at the Agricultural History Farm Park in Montgomery County, Maryland. Participants can choose from three timed challenges—3-hour, 6-hour, or 10-hour—where runners must complete one lap of the course each hour, resting o..

The More Miles Last One Standing Challenge is an endurance running event held in Knoxville, Maryland, featuring a unique "last one standing" format. Participants run a 4.167-mile loop, known as "the yard," every hour on the hour, continuing as long as they can complete the distance within the hour...

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..