Trail Running calendar near Annapolis 2025-2026

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 Sheetz-to-Sheetz Trail Run is a unique 14-mile untimed race held in King George, Virginia, designed to benefit local charities. Participants start at one Sheetz convenience store and finish at another, traversing the scenic Dahlgren Railroad Heritage Trail. The event emphasizes enjoyment over co..

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 Cancer Crushin' 5k is a charitable running event taking place at the Jacobus Lions Ambulance Building in Jacobus, PA. This event aims to raise funds for the American Cancer Society, promoting awareness and support for cancer research and patient care. Participants can register for the race at a..

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 Gunpowder Keg Ultra, hosted by the Baltimore Road Runners Club, features a scenic trail race in Gunpowder State Park, Parkton, MD. Participants can choose between a 25K or 50K distance, with the course consisting of a 15.5-mile loop of single track, fire road, and asphalt. Runners can switch dis..

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..

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 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..

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 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 Spencerville Adventist Academy 5K, 1 Mile Race, and Kids Fun Run is an annual event that promotes fitness and community engagement. Scheduled for May 4, 2025, this event features a 5K cross-country race, a 1-mile run, and a fun run for children aged 9 and under. Participants receive a compliment..

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 Race4Warriors Half Marathon is part of a larger event that includes 5K and 10K challenges, taking place in Lewes, Delaware. This event aims to support Wounded Warriors and homeless veterans while fostering connections between military and civilian communities. Participants can choose from variou..

The Dahlgren Trailblazer is an annual community bike event held in King George, Virginia. Participants embark on a friendly 8-mile ride starting from the trailhead at 10431 Bloomsbury Road, turning around at 9274 Comorn Road. The event is organized by the Friends of the Dahlgren Railroad Heritage Tr..

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..

The Conestoga Crusher 10K Trail Race, along with the Conestoga Cruiser 5K and the Kids Trail Race, will take place on May 17, 2025, at Kelly's Run Nature Preserve in Holtwood, PA. This event offers a thrilling experience for trail runners, featuring scenic routes through the Conestoga Trail and the..