Trail Running calendar near Leonardtown 2025-2026

The Wilderness Run 10k is a scenic cross-country trail race taking place at Wilderness Run Vineyard, located in the historic Chancellorsville and Wilderness battlefields. Participants can enjoy a challenging course with hills, wildlife sightings, and the option to fish by the pond. The event include..

The Fall Backyard Burn Trail Run at Lake Fairfax Park in Reston, VA, offers an exciting opportunity for runners to enjoy a scenic and challenging course. Participants can choose between a 5-mile or 10-mile race, featuring beautiful singletrack trails with minimal pavement and stunning views of the l..

The Patapsco Valley 50K is an annual trail running event held in Patapsco Valley State Park, Baltimore, MD. In 2025, the race will feature both a 50K and a 25K option, with participants receiving high-quality event shirts, unique finishers awards, and access to well-stocked aid stations. Runners can..

The Halloween Horror 10k is a thrilling running event taking place at Conway Robinson State Forest Park. Scheduled for October 26, 2025, participants can enjoy a scenic trail route that features technical terrain and minor hills. The event welcomes both runners and walkers, with a virtual race optio..

The Fall Backyard Burn Trail Run at Riverbend Park is a scenic trail running event scheduled for November 2, 2025, in Great Falls, Virginia. Participants can choose between two distances: a 5-mile or a 10-mile course, both featuring beautiful riverside singletrack and moderate elevation changes. The..

The MCRRC Stone Mill 50 Mile Run is a premier ultramarathon event taking place in Montgomery Village, Maryland. Scheduled for November 8, 2025, this challenging race attracts runners from various backgrounds, offering a scenic course that showcases the beauty of the local landscape. Participants can..

The Rosaryville Veterans Day Trail Race is an annual running event held at Rosaryville State Park in Upper Marlboro, Maryland. This race features two distance options: a 50K and a 20K, catering to both seasoned ultramarathoners and those looking for a shorter challenge. The event not only promotes p..

The Schaeffer Half Marathon and 10K Trail Run, organized by EX2 Adventures, takes place at the scenic Button Farm in Germantown, MD. This event features a challenging course known for its twisty singletrack and open farm field running, with distances of 6.7 miles for the 10K and 13.3 miles for the h..

The Fall Backyard Burn at Hemlock Overlook is a trail running event scheduled for November 16, 2025, in Clifton, Virginia. Participants can choose between two distances: a 5-mile or a 10-mile course, both set in the scenic 425-acre Hemlock Overlook park along the historic Bull Run. The course featur..

The Tuckahoe 25K is an exciting trail running event scheduled for November 22, 2025, in Queen Anne, MD. This race, organized by the Centreville Crushers and Algonquin Ultras Inc., offers a challenging yet accessible 25K course primarily on single-track and wider horse trails. Participants can expect..

The Fall Backyard Burn at Laurel Hill is a trail running event set in the scenic 1600-acre grounds of the former Lorton Reformatory in Lorton, Virginia. Participants can choose between a 5-mile or 10-mile course, featuring a mix of forested and open meadow singletrack trails. The race begins and end..

The 21st Annual Catonsville High School XC Turkey Trot is a cherished community event celebrating health and wellness. This year, participants can choose between a 1 Mile Family Fun Run and a 5K race, both of which are chip-timed. The event emphasizes community involvement, as all proceeds support t..

The Lake Anna Turkey Trot Half is a scenic running event held at Lake Anna State Park, featuring a half marathon, 10k, and 5k races. The half marathon course is a mix of 50% trail and 50% paved road, with a completion time limit of 3:15. Participants can also opt for a virtual race option.Runners re..

Devil Dog Ultras is an exciting trail running event held in Prince William Forest Park, Virginia, featuring three challenging distances: 100 miles, 100K, and 50K. The course consists of primarily single-track trails with some technical sections, and runners can expect well-stocked aid stations throu..

The Fall Backyard Burn Trail Run at Fountainhead Regional Park offers participants a choice between a 5-mile and a 10-mile race, set against the scenic backdrop of the Occoquan Reservoir in Fairfax Station, VA. Known for its beautiful hiking trails and challenging terrain, this event has been a favo..

The Pocahontas Half, along with a 10k and 5k, is a scenic running event held at Pocahontas State Park near Richmond. Participants can enjoy a beautiful forest trail that features a mix of dirt and pine needles, making for a softer running experience. The event welcomes walkers and offers a virtual r..

The Snowy Owl 10 Mile is a trail race held at York River State Park, featuring a challenging course that includes technical single track, dirt fire roads, and scenic views. Participants will navigate rocky sections and rolling terrain, with an elevation gain of approximately 600 feet. The event supp..