Trail Running calendar near Woodstock 2026-2027

A *100-mile* ultramarathon on the C&O Canal towpath near the Potomac River, run as one ~40-mile loop plus two ~30-mile loops. Aid stations appear every 3–6.9 miles and the event is a WSER 2027 qualifier.

A spring race at Third Winchester Battlefield Park on April 25 2026 offering 5K 10K and a Half Marathon, with walkers welcome and virtual entry options that include medal or shirt packages.

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.

Experience the fourth annual trail run at Mount Aetna Adventist School in Hagerstown. Choose between a 3k or 5k course to support student projects and enjoy fitness within a community setting.

Farm Park Challenge is a trail running event at the Agricultural History Farm Park in Derwood, Maryland on May 2, 2026. Options include a marathon, a 25K, and timed three hour six hour and ten hour challenges run as five mile laps.

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.

A community 5K and 10K in Rock Creek Park on May 2, 2026, organized by Rock Creek Conservancy. The event blends trail and road running with guided tours, awards, and activities while supporting park restoration and future improvements.

A trail run on May 2, 2026 at 10709 Gunston Rd in Lorton offering a Fun Run, 5K, 10K and virtual options. Proceeds support no-cost enrichment programs at Gunston Elementary School.

Trail half marathon and 10K at Fountainhead Regional Park near Washington D.C. Courses feature singletrack with rocks and roots, stream crossings, multiple aid stations, and notable climbs, with chip timing and postrace support.

A timed mountain-trail race at Mint Springs Valley Park in Crozet, covering about 3.9 miles with 860 ft of elevation gain. The single-track ridge course finishes by the upper lake and includes overall and age-group awards.

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.

Experience four distinct trail races across Charlottesville and Crozet in this summer series. Compete for age group awards and finisher shirts while running through scenic venues like Mint Springs and Pen Park.

A 100 mile trail ultramarathon in the Massanutten Mountains with rocky terrain and over 18,000 feet of ascent, starting and finishing at Caroline Furnace in Virginia’s Shenandoah Valley. A 36 hour cutoff applies and training runs are held b..

Experience a fast and flat race along the historic Chesapeake and Ohio Canal Towpath in Potomac. With 5k, 10k, and half marathon distances available, walkers and runners of all kinds are welcome at Carderock Park.

Join the Ed Poling Memorial HARC Hike for Hunger & Hope, now in its 14th year. Choose from scenic C&O Canal Towpath hikes in May or a challenging Appalachian Trail hike. This fundraising event supports local community programs.

An evening 5 km and 10 km run through the historic Manassas National Battlefield with start and finish at The Winery at Bull Run in Centreville, VA. In-person and virtual entry options are available.

Run or walk a scenic off road 5K course along the Cacapon River and Lewis Farm. This benefit event supports local youth programs while celebrating the Wardensville Spring Fest with local food and creativity.

A backyard ultra at Mustang Trailhead offering a 24 hour 100 mile limit and a 12 hour after dark 50 mile option. One hour loops of about 4.167 miles with a single aid station providing water Gatorade and snacks.