Trail Running calendar near Leonardtown 2025-2026

The Patapsco Valley 50K is an annual trail running event held at Patapsco Valley State Park near Baltimore, Maryland, with race headquarters at CCBC-Catonsville. The event features two distances: a 50K and a 25K, both available as in-person or virtual races. Runners enjoy a scenic, historic, and wel..

The Greensprings 24 is a 24-hour endurance race held in Williamsburg, VA, benefiting The Arc of Greater Williamsburg, a nonprofit supporting adults with disabilities. The race features a USATF-certified 2.215-mile loop course on mainly flat, scenic, crushed gravel trails with minimal elevation chang..

The Halloween Horror 10k is a trail running event held at Conway Robinson State Forest in Gainesville, Virginia. The course features a loop through forest trails with some technical terrain and minor hills, with the 10k consisting of two laps of the 5k route. The event welcomes both runners and walk..

The Fall Backyard Burn Trail Run at Riverbend Park in Great Falls, VA, is a scenic trail running event featuring 5-mile and 10-mile race options. Set adjacent to the Potomac River and near Great Falls National Park, the course offers beautiful riverside singletrack trails with a few short hills and..

The MCRRC Stone Mill 50 Mile Run is a challenging trail ultramarathon held in Montgomery Village, Maryland. The 50-mile course features scenic routes along the Seneca Greenway and Muddy Branch trails, traversing forested, rolling terrain primarily on single-track dirt paths. Runners encounter small..

The Schaeffer Half Marathon and 10K Trail Run, hosted by EX2 Adventures, takes place at the scenic Button Farm in Germantown, Maryland. This event features two distances: a 13.3-mile half marathon and a 6.7-mile 10K+, both offering challenging courses with twisty singletrack trails and wide-open far..

The Rosaryville Veterans Day Trail Race, hosted by Annapolis Striders, is an annual trail running event held at Rosaryville State Park in Upper Marlboro, Maryland. The 16th edition in 2025 features two distances: a 50K ultra and a 20K race. Both courses loop around a 9.5-mile single-track perimeter..

The Fall Backyard Burn Trail Run at Hemlock Overlook in Clifton, VA, is a scenic trail running event featuring 5-mile and 10-mile race options. Set in a 425-acre park along the historic Bull Run, the course offers a mix of hiking trails, old dirt roads, stream crossings, grassy fields, and minimal p..

The Tuckahoe 25K is an annual trail running event held in Queen Anne, Maryland, featuring a 25-kilometer (15.5 miles) course primarily on single-track and horse trails. The terrain includes runnable hills, some rooty and muddy sections, but is not overly technical, making it suitable for both newcom..

The Fall Backyard Burn at Laurel Hill is a trail running event held at the Workhouse Arts Center in Lorton, VA, set on the scenic 1600-acre grounds of the former Lorton Reformatory. The course features a mix of forested and open meadow singletrack trails composed of dirt and crushed stone, with mini..

The Winery at Bull Run Turkey Trot is a scenic trail run held at the Manassas National Battlefield, featuring 5k and 10k options. Participants enjoy running through historic Civil War sites on dirt trails, cross-country paths, and gravel terrain, with some hills along the course. The event benefits..

The 21st Annual Catonsville High School XC Turkey Trot, held in Catonsville, Maryland, is a cherished community event celebrating health, wellness, and family. It features a cross country-style 1 Mile Family Fun Run and a 5K race, both chip timed. The event fosters a spirited atmosphere with awards..

The Lake Anna Turkey Trot Half is a scenic and challenging race held at Lake Anna State Park, featuring a half marathon, 10k, and 5k courses. The half marathon is an out-and-back trail race with a 3-hour and 15-minute time limit, while the 10k and 5k courses combine trail and paved roads. Participan..

The 27th Milford Cross Country Booster Reindeer Stampede 5k is a festive running event held at Killens Pond State Park in Felton, Delaware. This 5k run/walk features chip timing with MYLAPS BibTag and offers competitive walking and running categories. Participants receive long sleeve tee shirts and..

Devil Dog Ultras is a challenging trail running event held in Prince William Forest Park near Triangle, Virginia. It offers three race distances: 100 miles, 100K, and 50K. The course features primarily single-track trails with some roots, rocks, and brief technical sections, along with fire roads an..

The Fall Backyard Burn Trail Run at Fountainhead Regional Park in Fairfax Station, VA, is a popular trail running event held on December 7, 2025. The race offers two challenging distances: a 4.8-mile loop with 450 feet of elevation gain and a tougher 10.5-mile course featuring an additional out-and-..

The Pocahontas Half is a scenic running event held at Pocahontas State Park in Chesterfield, Virginia. It features a half marathon, 10k, and 5k race, all taking place along the forested Bright Hope Trail. The course offers a soft running surface of dirt and pine needles with some minor hills, provid..

The Tinsel Trot 10k in Louisa, VA, is a festive cross-country running event held at Southern Revere Cellars. The course loops around the winery property, with the 10k consisting of four laps and the 5k two laps, featuring gentle terrain without major hills. Participants receive a technical event shi..

The Snowy Owl 10 Mile is a challenging trail race held at York River State Park in Williamsburg, Virginia. The course features a mix of terrain including five miles of technical single track, dirt fire road trails, about three-quarters of a mile on paved road, rocky sections, twisting trails, and a..

The Mid-Maryland Trail Festival 50k is a 31-mile ultramarathon held at Rockburn Branch Park in Elkridge, Maryland. The course consists of six loops, each approximately 5.179 miles, winding through wooded trails. Participants can run the full 50k solo or form relay teams of 2 to 6 members, exchanging..