Trail Running calendar near Winchester 2025-2026

The Rosaryville Veterans Day Trail Race, hosted by the Annapolis Striders, is a celebrated annual event taking place at Rosaryville State Park in Upper Marlboro, Maryland. This year marks the 15th edition of the race, featuring both 50K and 20K distances. The course offers a scenic and challenging e..

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 fields, offering participants a unique running experience. The half marathon co..

The MCRRC Stone Mill 50 Mile Run is a challenging trail running event set in Montgomery County, Maryland, showcasing the scenic Seneca Greenway and Muddy Branch trails. Participants navigate a primarily single-track dirt course featuring forested terrain and small stream crossings, with some areas p..

The Fall Backyard Burn Trail Run at Hemlock Overlook is a scenic 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 featuring a mix of forested fire roads, hiking trails, and open fields. The ra..

The Fall Backyard Burn at Laurel Hill is a trail running event hosted by EX2 Adventures, taking place at the scenic Workhouse Arts Center in Lorton, Virginia. Participants can choose between a 5-mile or 10-mile course that winds through a mix of forested and open meadow singletrack across 1,600 acre..

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 is a cherished community event celebrating health and wellness. Scheduled for November 27, 2025, this event features a 1 Mile Family Fun Run and a 5K race, both of which are chip-timed. Participants can enjoy a family-friendly atmosphere while s..

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..

Devil Dog Ultras is an exciting trail running event held in Prince William Forest Park, Virginia, featuring 100-mile, 100K, and 50K races. The course consists of primarily single-track trails with some technical sections, and runners can expect well-stocked aid stations throughout the loops. Partici..

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 Mid-Maryland Trail Festival 50k is an exciting running event taking place in Elkridge, MD, featuring a challenging 31-mile course comprised of six loops through scenic wooded trails. Participants can choose to run the entire 50k solo or form relay teams of up to six members to share the distance..

The ICY-8 Spotsylvania Courthouse is an exciting trail running event taking place at Lake Anna State Park in Spotsylvania, VA. Scheduled for February 7, 2026, this event features an 8-hour adventure trail run and a new Half Marathon+ option. Participants can choose from various loop distances, inclu..