Trail Running calendar near Winchester 2024-2025

The Drumstick Dash Turkey Trot features a 5k and an 8-mile race, celebrating the Thanksgiving holiday with a festive running event. Participants can enjoy a scenic, flat course along the Mount Vernon Trail, suitable for walkers and strollers. Runners receive a finisher's medal, a technical event shi..

The Winter Lake Anna Half is a scenic running event held at Lake Anna State Park, featuring a half marathon, 10k, and 5k courses. The half marathon consists of a mix of trail and paved road, with a time limit for completion. Participants receive a finisher's medal, a technical event shirt, and enjoy..

Devil Dog Ultras is a trail running event held at Prince William Forest Park in Triangle, VA, featuring 100-mile, 100K, and 50K races. The course consists of primarily single-track trails with some technical sections, fire roads, and rolling hills. Runners will navigate loops of varying lengths, wit..

The Fall Backyard Burn Trail Run at Hemlock Overlook is scheduled for December 8, 2024, in Clifton, VA. This event features two race distances: a 5-mile and a 10-mile trail run, set in a picturesque 425-acre park along the historic Bull Run. The course includes a mix of hiking trails, dirt roads, an..

The 2024 Santa's Summit 7k & 7.5 Miler takes place at Bull Run Marina, featuring a scenic and challenging course along the Bull Run Occoquan Trail. Participants can choose between two distances, with both events contributing points to year-long running series. Runners will receive a finisher's medal..

The Leesylvania 10k is a trail running event taking place at Leesylvania State Park, featuring a scenic course with some hills and a small staircase. Participants can earn points towards the Year-Long 5k, 10k, and Winter Series. Runners receive a finisher's medal, a technical event shirt, and chip t..

The Mid-Maryland Trail Festival features a challenging 50K race, consisting of six loops of approximately 5.179 miles each, set in a scenic wooded trail. Participants can choose to run the entire distance solo or form relay teams of up to six members to share the challenge. The event, taking place a..

The Winter Conway Robinson 10k is a trail running event taking place at Conway Robinson State Forest Park. Participants can enjoy a scenic loop route featuring technical terrain and minor hills. The event includes both a 10k and a 5k option, with points contributing to various series standings.Runne..

The ICY-8 event in Spotsylvania, VA, is an exciting trail running adventure that offers participants the chance to challenge themselves in a beautiful natural setting. Scheduled for February 1, 2025, this event features a unique format where runners can choose from multiple loops, including a new IC..

The Trail Demon 10k is a challenging and scenic running event taking place at Dirt Farm Brewing in Bluemont, Virginia. Participants will navigate a technical course featuring hilly terrain, tree roots, and rocks, offering stunning views and a rewarding experience. Runners will receive a finisher med..

The Dark Side 8 Hour Ultra is an exciting trail running event held at Little Bennett Park in Clarksburg, MD. Participants can run a 5.5-mile loop on scenic single track trails for a total of eight hours, making it suitable for both competitive runners and those looking to enjoy the outdoors. The eve..

No Man's 50K is a unique trail running endurance challenge designed exclusively for women, with distances of 25K and 50K. Established in 2016, the event aims to promote female participation in trail races, inspired by a young girl's observation about the lack of women in such events. The race featur..

The MCRRC Seneca Creek Greenway Trail Marathon & 50K is a running event scheduled for March 8, 2025, in Gaithersburg, Maryland. This event offers participants the choice between a marathon and a 50K race, catering to various levels of endurance and experience. The race takes place on scenic trails, ..

The Hone Quarry Ultra is a challenging 40-mile trail endurance race set in the picturesque Shenandoah Valley, starting and finishing at Briery Branch. Participants will navigate through the George Washington National Forest, encountering stunning landscapes, including cliffs, meadows, and waterfalls..

The Bull Run Run 50 Miler is a challenging trail running event held in Clifton, Virginia, featuring a scenic 50-mile course that follows the Occoquan River and the historic Bull Run. Set against a backdrop of rolling forested terrain, the race takes place during the peak of spring, showcasing stunni..

The Chopawamsic Challenge is an exciting 50K and 100K trail race held in Prince William Forest Park, Virginia. This event offers a unique opportunity for runners to test their endurance on scenic trails with significant elevation changes, featuring over 6,000 feet of ascent and descent for the 50K a..

Run to Remember is a commemorative running event held at Piney Run Park in Sykesville, MD, featuring multiple race options including a 50K, 50K Relay, 25K, 5 Miler, and an 8 Hour Challenge. This event honors the memory of cherished members lost, encouraging participants to challenge themselves in th..

The Spring Third Winchester Battlefield Half is a scenic running event taking place at the historic Third Winchester Battlefield. Participants can choose from a half marathon, 10k, or 5k, with options for both in-person and virtual participation. Runners will receive a finisher’s medal, a technical ..

The "On The Dam Trail: Quemahoning Relay Race" is a challenging running event set in the scenic environment of Camp Harmony, Hooversville, PA. Participants can choose between a 50K solo run, a 50K relay for teams of four, or a 30K solo option. The course features a mix of single track trails, stream..

The C&O Canal 100 is a challenging 100-mile ultramarathon set along the scenic C&O Canal towpath in Maryland. The race features a unique course layout consisting of one approximately 40-mile loop and two 30-mile loops, making it suitable for both novice and experienced runners. Participants will enc..