Trail Running calendar near Woodstock 2025-2026

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 Wisdom Oak Winery 10k is a scenic running event held at the picturesque Wisdom Oak Winery, featuring a challenging cross-country course that includes rolling hills and gravel roads. Participants can enjoy a glass of wine post-race, along with a finisher's medal and a technical event shirt. The e..

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 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 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. Participants can choose between two distances: a 5.7-mile or a 10.1-mile course, both set against the scenic backdrop of Gunston Cove and the adjacent Mason Neck National Wildlife Refuge..

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..

The Perfect Day 50K is a running event taking place in Keezletown, Virginia, on May 3, 2025. Participants can choose to compete individually or as part of a team, with options for teams of two or three. This event is designed for runners of various skill levels, promoting a fun and competitive atmos..

The Mint Springs Trail 5K is an annual running event held at Mint Springs Valley Park in Crozet, Virginia. This challenging 3.1-mile course features scenic mountain trails, steep climbs, and beautiful views, making it suitable for runners of all experience levels, as well as families and walkers. Pa..

The Four Leaf Clover Project's Run for Prosperity is a scenic 5k event taking place at Bluemont Station Brewery & Winery. Participants can enjoy a chip-timed race, with awards for top finishers in various categories. The event also includes a fun run and offers a virtual race option for those unable..

The Historic Waterford Trail Run/Walk is an outdoor event taking place in Waterford, Virginia, on May 10, 2025. Participants can choose from a 5K Trail Run/Walk, a 10K Trail Run/Walk, or a Fun Run, all set against the scenic backdrop of Western Loudoun County. The course features a mix of trails, pa..

The Ed Poling Memorial PA Challenge is a demanding hiking event that covers over 20 mountainous miles on the Appalachian Trail in Pennsylvania, starting at Caledonia State Park and concluding at Pen Mar Park. Participants receive comprehensive support, including lunch, snacks, drinks, and transporta..