Trail Running calendar near Woodstock 2026-2027

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.

Join the inaugural Run Rock Creek 5K/10K in Washington D.C. to experience a forest run through America’s premier urban national park while supporting vital trail restoration and conservation efforts.

Participate in a scenic trail run in Lorton to support Gunston Elementary School. This community event features 10K, 5K, and Fun Run distances with proceeds funding student enrichment and arts programs.

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 of Virginia with over 18,000 feet of ascent, a 36 hour cutoff, and organizational support including a Participants’ Guide, training runs, and volunteer staffing.

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.

Join the 14th annual Hike for Hunger & Hope with two events. Choose a challenging 10 or 20-mile Appalachian Trail hike in May or a scenic 5K/10K on the C&O Canal. All hikes support local food programs and refugee services.

Experience an evening run through the historic Manassas National Battlefield with the Night Raider 5k and 10k. Finish your race at The Winery at Bull Run and enjoy a post-race gathering at this scenic Virginia vineyard.

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.

Test your endurance at Furbutt’s Backyard 24 Hour where runners complete a 4.167 mile loop ogni hour on a scenic trail course. Whether you aim for 24 hours or the nighttime 12 hour option, this event focuses on community and persistence.

Experience a downhill 3 km run through the scenic quartzite ridges of Seneca Rocks. This free gravel road event crosses the Potomac River as part of the Fourest Festival celebrations.

A backyard ultra at Manidokan Camp in Knoxville, MD on May 30, 2026, featuring official 4.167 mile laps and a 1 mile 24 hour event. On-site camping, aid station, showers, timing, shirts, and cash prizes for the winner and the assist.

A loop course at Sky Meadows State Park on May 31, 2026 offering 5K and 10K distances plus virtual options. The route passes fields, streams and sometimes cows, and walkers are welcome.

Experience the FXBG Trail 5 Miler at Motts Run Reservoir in Fredericksburg. This five mile trail race features three distinct climbs and over 300 feet of elevation gain along a scenic and flowing course.

A measured 100 miles loop through the Massanutten Mountains and Shenandoah River Valley featuring 14 climbs and about 14,000 feet of gain. The mixed road and trail course has a 24 hour cutoff to earn the silver buckle.

This 45th annual memorial race honors coach Gary Brown with a fast, flat five-mile out-and-back on the shaded C&O Canal Towpath. Participants receive chip timing, a tech shirt, and awards. A student entry option is available for this Willia..