Trail Running calendar near Winchester 2025-2026

The Battle of Kelly's Ford is a cross-country running event taking place at the scenic Kelly's Ford Inn in Remington, Virginia. Participants can choose between two races: a 6Km race for women and girls, and an 8Km race for men and boys. The course features a 2Km loop that combines close-cut grass an..

The Hone Quarry Ultra is a challenging 40-mile trail endurance race set in the picturesque Shenandoah Valley, starting and finishing at Briery Branch. Participants will navigate through the George Washington National Forest, experiencing stunning landscapes, including cliffs, meadows, and waterfalls..

The Smoketown Brewery 10k is a scenic running event taking place on March 30, 2025, near Smoketown Brewery in Brunswick, MD. Participants can enjoy a flat, light gravel dirt path while competing for points in the Year-Long 5k, 10k, and Sippin Series. The event welcomes walkers and offers a virtual r..

The 1781 Brewery 10k is a scenic cross-country trail run taking place at the historic 1781 Brewing Company, located on the Chancellorsville and Wilderness battlefields. Participants can enjoy a challenging course with hills, and both runners and walkers are welcome. Each participant receives a finis..

The Bull Run Run 50 Miler is a challenging trail running event held in Clifton, Virginia, set to take place on April 5, 2025. This 50-mile race winds through a picturesque linear park that follows the Occoquan River and the historic Bull Run, showcasing the area's natural beauty during spring. Parti..

The Massanutten King of the Mountain 18 Miler is an exciting running event set in McGaheysville, Virginia. This challenging course features a mix of trails, gravel, and roads, offering participants scenic views and significant elevation gain. Starting at Massanutten Base Camp, runners will traverse..

The Breeze Thru the Trees 5k is a cross-country running event taking place at Ruppert Nurseries in Gaithersburg, Maryland. Scheduled for April 6, 2025, the event features a 5K run and a 1-mile fun run, set against the backdrop of a lush tree nursery in Montgomery County’s Agricultural Reserve. Proce..

The Wild Trail 10K in Thurmont, MD, is a beginner-friendly trail race set in the scenic Thorpewood property. Scheduled for April 6, 2025, this event offers participants a unique opportunity to experience a beautiful course that is otherwise private. The race is part of the FSRC Grand Prix and is fre..

The Spring Backyard Burn Trail Run at Lake Fairfax, scheduled for April 6, 2025, offers participants a choice between a 5-mile and a 10-mile race. Set in Reston, Virginia, the event features scenic trails with minimal pavement, showcasing beautiful views of Lake Fairfax. The course includes a mix of..

The Buck Ridge Burn Trail Races, taking place from April 6 to April 29, 2025, in Gardners, PA, offers a variety of trail running events including a Half Marathon, 10K+, 5K-ish Trail Race, and a Fun Run. Participants can also opt for virtual events, allowing them to run from their local trails. The c..

The Chopawamsic Challenge is an exciting 50K and 100K foot race held in Prince William Forest Park, designed for both seasoned ultra-marathoners and those looking to extend their trail running experience. The event features a scenic course with over 90% single-track trails, offering significant elev..

The C&O Canal 100 is a 100-mile ultramarathon set along the scenic Potomac River, ideal for both first-time and experienced runners. The course features a combination of one 40-mile loop and two 30-mile loops on the historic C&O Canal towpath, providing beautiful riverside views and a smooth terrain..

The On The Dam Trail: Quemahoning Relay Race is a challenging running event taking place at Camp Harmony in Hooversville, PA. Participants can choose between a 50K solo run, a 50K relay for teams of four, or a 30K solo option. The scenic course features rolling hills, stream crossings, and dense pin..

Run to Remember is a commemorative running event held in Piney Run Park, Sykesville, MD, featuring various race options including a 50K, 50K Relay, 25K, 5 Mile, and an 8 Hour Challenge. This event honors the memory of lost loved ones and encourages participants to challenge themselves in their honor..

The Winchester Battlefield Half is a scenic running event taking place at the Third Winchester Battlefield, featuring a half marathon, 10k, and 5k. Participants can enjoy a chip-timed race with a technical event shirt and a finisher's medal. The event promotes awareness for organ donation through Te..

The Spring Backyard Burn Trail Run at Pohick Bay is a thrilling trail running event scheduled for April 27, 2025, in Lorton, Virginia. Participants can choose between two distances: a 5-mile or a 10-mile course, both featuring a mix of forested fire roads, hiking trails, and scenic views of Gunston..

Mount Aetna Adventist School's Fun Trail Run is an exciting annual event that promotes fitness and community spirit. Scheduled for April 27, 2025, in Hagerstown, MD, the event features various running options, including 5k and 3k races for both adults and children. Participants can also register as..

The Lost River Trail Run is an exciting running event set in the scenic Lost River State Park in Mathias, West Virginia. Participants can choose from various distances, including a 1 Mile Run/Walk, 4.5 Mile Run, 9 Mile Run, and a Half Marathon (13.1 miles). The course features a mix of hilly terrain..

The Farm Park Challenge is an exciting running event taking place at the Agricultural History Farm Park in Derwood, Maryland. Participants can choose from various challenges, including a marathon, a 25K, and timed events of 3, 6, or 10 hours, all featuring a 5-mile loop course. Runners start each lo..

The Run First Wine Later 5k, taking place at Creek’s Edge Winery, offers participants a scenic cross-country experience through the vineyard. This event includes both a 3k and 5k race, contributing points to the Year-Long 5k & Back of the Pack Series as well as the Sippin’ Series. Runners will recei..