Trail Running calendar near Winchester 2026-2027

This event offers trail races in Pennsylvania's Michaux State Forest or a virtual run on your own trail. Choose from a half marathon, 10K+, or 5K-ish distance. All finishers get a unique handmade coaster, and awards are given for top in-per..

Run a fast and flat course along the C&O Canal Towpath in Maryland's Carderock Recreation Area. Choose from a 5K, 10K, or Half Marathon distance, with walkers welcome. The event also offers a virtual participation option.

Run to Remember is a multi-distance trail event held in Sykesville's Piney Run Park. Runners traverse a scenic 5.25-mile loop past woods, meadows, and a lake. The event honors lost loved ones and supports cancer research.

Experience a cross-country style 5k at the scenic Hauser Hill Event Center. Registration includes a t-shirt, wine glass, unique finisher medal, and a wine pour. The course offers beautiful views but is not flat, and walkers, dogs, and virtu..

Run Fest at Panorama Farms offers a day of trail racing and community celebration on April 18, 2026. Choose from a 4-mile trail race, a team relay, or a 1-mile fun run, followed by a festival with live music and local food. It's a chance to..

Run through the scenic vineyards of Barrel Oak Winery on a challenging cross-country course with hills and gravel paths. Runners receive a finisher's medal, tech shirt, and a glass of wine, with proceeds supporting veterans. A virtual optio..

This trail run takes place on the scenic singletrack at Lake Fairfax Park in Reston, VA. Choose from a 5.1 or 10-mile course with rolling terrain and lake views. The event includes post-race food, a free kids race, and optional child care.

Experience a scenic 5K cross country race through the hop yards and vineyards of Red Shedman Brewery. Finishers enjoy a complimentary beverage at this unique farmhouse event in Mount Airy.

Run 100 flat miles on the scenic C&O Canal. This April event starts and finishes at Camp Manidokan and is a Western States qualifier. Finishers get a belt buckle and enjoy a post-race meal.

Run a scenic loop course on the light gravel trails of Third Winchester Battlefield. Choose from 5k, 10k, or half marathon distances, with chip timing, medals, and shirts for all participants. Points count towards annual series, and walkers..

Event Overview The On the Dam Trail: Quemahoning Relay Race takes place on Saturday, April 25, 2026. It features several race options: a 50K solo, a 50K 4-person relay, a 30K solo (one lap), and a 10K. The 50K solo and 4-person relay, as we..

Experience a unique trail race through an active rock quarry at the Luck Stone Leesburg Plant. This 5K event supports environmental preservation and features family activities and awards for all ages.

An annual 5K at Marymount University on April 25, 2026, run on the Bluemont and Custis Trails with a post-race gathering, a virtual option, chip timing, and guaranteed shirts for early registrants.

Run a scenic 5k around the Bluemont Station Brewery property in Virginia. The event welcomes both runners and walkers and offers in-person and virtual participation options.

A 5K trail run and walk on private property near Amissville, Virginia, benefiting the Chefs For Kids Foundation. The mostly dirt course has gentle hills; registration includes a race T-shirt, bib, and post-race refreshments.

A trail running event at Agricultural History Farm Park in Derwood, Maryland, featuring timed lap challenges where each lap must finish in under an hour and also offering a marathon and 25K.

The Perfect Day 50K takes place on the Massanutten Western Slope in Keezletown, Virginia. Runners can compete individually or as part of a two or three person team on a Saturday in May. The event offers a full day on the trails.

Trail runners take on the scenic and challenging courses of Fountainhead Regional Park. Distances include a half marathon and a 10K, featuring the Bull Run Occoquan Trail and notable hills. The event also hosts the Collegiate Running Associ..

The Johnnycake Jolt Series is a four-week trail run event on Wednesday evenings in May. Runners can tackle a scenic 10 km course in the Pickall Area of Patapsco Valley State Park. It’s a grassroots series designed to bring the local running..

A multi distance trail event in Waterford VA on May 9, 2026 that runs through historic village streets, vineyards, trails and unpaved roads. Proceeds support the Waterford Foundation and 5K and 10K finishers receive a shirt and medal.