Trail Running calendar near Woodstock 2026-2027

A 100 mile trail ultramarathon in the Massanutten Mountains near Fort Valley, Virginia, featuring rocky terrain, short rugged climbs with more than 18,000 feet of ascent and a 36 hour cutoff.

A towpath race at Carderock Park in Potomac, MD on May 16, 2026, offering 5K, 10K and half marathon distances; courses are described as fast and flat, walkers are welcome, and virtual entry options include medal and shirt choices.

Two days of fundraising hikes in May 2026 offer 5K and 10K canal routes plus 10 and 20 mile Appalachian Trail challenges, with trail support, fundraising matches, and proceeds benefiting Micah’s Backpack and the Refugee Welcome Network.

A two-part fundraising hike in May with Challenge options on the Appalachian Trail and 5K/10K hikes on the C&O Canal, supporting Micah’s Backpack and the Refugee Welcome Network; individual fundraising is matched 2-to-1.

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.

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 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 loop race at Sky Meadows State Park on May 31, 2026, offering 5 km and 10 km in-person distances plus virtual entry options, with a scenic course around Turners Pond featuring fields and streams.

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.

A community team race at Burke Lake Park on June 6, 2026 featuring a 5K race and a 2K walk and roll that raises funds for services and advocacy for people with intellectual and developmental disabilities.

A cross-country 5k and 1 Mile at Merrie Mill Farm and Vineyard in Keswick, VA on June 7, 2026. Post-race participants have access to a reserved cabana and a gift basket raffle with at least a $200 prize.

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.

A Juneteenth trail event in Germantown on June 19, 2026 offering 6K and 12K courses around Button Farm and the Schaeffer Farm Trails, with virtual options and tiered registration fees.

A 40 mile trail run in Davis, West Virginia on June 20th, 2026 that crosses Monongahela National Forest and Dolly Sods. The 22nd edition covers plateau terrain, bogs, woodland paths, and rocky plains.

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.