Trail Running calendar near Winchester 2026-2027

A trail run and walk through historic Waterford VA on May 9, 2026 featuring 5K, 10K, a kids mile fun run and virtual options, with shirts, medals and awards for top finishers.

A Mother's Day 5k and 10k in Silver Spring, Maryland, held by Swift Running with a course that passes through Martin Luther King Jr. Recreational Park. The event offers in person and virtual entries with tiered registration fees.

A four-date series of 10K trail runs in the Pickall Area of Patapsco Valley State Park from May 6 to May 27, 2026, with running time results and options to enter single dates or the full series.

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.

A four-date series of 10K trail runs in the Pickall Area of Patapsco Valley State Park from May 6 to May 27, 2026, with running time results and options to enter single dates or the full series.

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 31.9-mile trail 50K at Cowans Gap State Park on May 24, 2026, with about 5,800 feet of climb on the Tuscarora Trail. Entry is limited to 75 and requires prior ultramarathon experience.

A four-date series of 10K trail runs in the Pickall Area of Patapsco Valley State Park from May 6 to May 27, 2026, with running time results and options to enter single dates or the full series.

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 100-mile, 10-loop event on Rock Creek Trail near Washington D.C., with about 8,200 ft total elevation and a 36-hour cutoff. Two ticket types are listed at the same price including tax.

Trail run and walk on May 30, 2026 at Gentle Giants Draft Horse Rescue in Mt. Airy, MD featuring 1 mile and 5K courses across forest trails and open pasture with draft horses on the farm.

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.