Trail Running calendar near Woodstock 2026-2027

Evening 5k and 10k through the historic Manassas National Battlefield with start and finish at The Winery at Bull Run in Centreville, VA. In-person and virtual options are offered, with some virtual packages including medals or shirts.

A 5K run and walk beside the Cacapon River during Wardensville Spring Fest, supporting the Junior Crew program at Farms Work Wonders with age-division awards and same-day registration available.

Furbutt's Backyard uses a 4.167 mile hourly loop with a 24 Hour 100 mile limit and a 12 Hour After Dark option at Mustang Trailhead. A single aid station supplies water, ice, Gatorade and snacks and crews are allowed there.

A 3 km downhill run at Seneca Rocks during the Fourest Festival. The mostly gravel course follows Roy Gap Road between quartzite ridges and crosses the Potomac River, starting at Fourth Moon Camp and finishing at the Seneca Rocks Discovery..

A 5k run and walk on May 25, 2026 at the historic Stoke estate in Middleburg, featuring open fields, rolling hills and forest along Little River. The course includes rugged, uneven terrain; children 12 and younger must be with an adult.

A backyard ultra in Knoxville, Maryland where runners complete a 4.167 mile yard each hour until only one finishes. The event includes a 1-mile option, offers prize money for top finishers, and serves as a Backyard Ultra qualifier.

A scenic loop at Sky Meadows State Park on May 31, 2026, offering 5K and 10K courses with views of fields, streams and Turners Pond. Walkers are welcome and virtual entries are available with medal and shirt options.

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 mile loop through the Massanutten Mountains near Fort Valley, Virginia, featuring 14 significant climbs and mixed terrain. Runners have 24 hours to earn the silver buckle and 28 hours to finish.

A longstanding five-mile memorial run on the C&O Canal Towpath in Williamsport, MD, held June 6, 2026, with regular and student entries, chip timing, technical T-shirts, and awards for podium finishers.

The Arc of Northern Virginia Community Challenge at Burke Lake Park on June 6, 2026 features a 5K race and a 2K fun walk and roll. Teams raise funds to support services and advocacy for people with intellectual and developmental disabilitie..

A cross country 5K and 1 Mile at Merrie Mill Farm and Vineyard in Keswick on June 7, 2026, with in person and virtual options, a reserved post race cabana for participants, and a gift basket raffle.

A single-track trail race behind Zehmer Hall in Charlottesville covering about 3.1 miles, with steep climbs, technical footing, timing and bibs, and prizes for top finishers.

A night trail event in Prince William Forest Park featuring a 50 mile race made of two 25 plus mile loops, plus 25 mile and 10 mile options. The course is mostly single track with staffed aid stations and defined crew and pacer rules.

A community 5K and 1 mile Fun Run in Warrenton, VA that raises funds for Fauquier Education Farm, a 501(c)(3) that advances agricultural education and donates its harvest to local food banks.

Trail races on June 19, 2026 in Germantown, MD offering 6K and 12K courses around Button Farm and the Schaeffer Farm Trails. Walkers and several virtual entry options are available.

Experience a 40 mile ultramarathon through the Monongahela National Forest and Dolly Sods Wilderness. This trail run features the natural beauty of West Virginia with a route based around the Canaan Valley Resort State Park.

A blue-blazed out-and-back trail event near Frederick, MD offering 50K and 25K options on rocky, shaded trails with stream crossings, mandatory hydration, limited entries and staffed aid stations.

PUSO 5k & 10k on June 20, 2026 follows the Chesapeake & Ohio Canal path in Georgetown, Washington, DC. Runners and walkers can choose either a 5 km or 10 km distance, with registration fees varying by period.

Trail race on the Promised Land Trail behind Canaan Valley Resort offering a one-loop 5.9 mile and a two-loop 11.8 mile option. The field is limited to 200 participants and entrants receive a T-shirt and finisher medal.