Trail Running calendar near Winchester 2026-2027

This 50k trail race features a six-loop course through wooded trails at Rockburn Branch Park. Runners can tackle the full distance solo or form a relay team of up to six people to share the loops. An aid station provides fuel and hydration..

The No Man's 50K Challenge is a women's trail running event with 25K and 50K distances on a mixed-surface course in Virginia. It features a supportive atmosphere and a generous 9-hour cutoff. The race is limited to 120 entrants.

The Winter Conway Robinson 5k & 10k takes runners through the trails of Conway Robinson State Forest Park in Gainesville, Virginia. The event, scheduled for March 7, 2026, welcomes both runners and walkers and offers on-site and virtual par..

Explore Montgomery County's single-track trails at this low-key event in Seneca Creek State Park. Choose your challenge on race day: stop at the marathon finish or push on for the 50K. All runners get a tech shirt, medal, and a course with..

This cross-country run takes participants on scenic 3k and 5k courses around Creek’s Edge Winery in Lovettsville, VA. Walkers are welcome, and post-race wine tasting is part of the experience. The event also offers virtual participation opt..

The Naked Creek Trail Race offers 25K and 10K courses on the private, scenic trails of Panorama Farms in Virginia. Runners can experience wooded singletrack with views of the reservoir and Blue Ridge Mountains. The event provides a unique c..

A 5k and 10k at Smoketown Brewery on March 8 with out and back gravel courses, limited water stations, a virtual option, chip timing, a finisher medal, a technical shirt and a postrace beer.

A free International Women’s Day endurance day at Beaverdam Reservoir Park featuring a 7.5-mile loop and varied trail surfaces. The event centers women, offers course support through sunset, and focuses on movement and mutual support.

The Spring Backyard Burn Trail Run offers a scenic 5.4 or 10 mile course through the historic grounds of Laurel Hill Park in Lorton. The route features gentle, non-technical singletrack with rolling hills. A free kids race and post-race foo..

A cross country 4k and 8k around Twisted Oak Farm Brewery in White Post, VA with chip timing, water stations, and a virtual option. Points count toward multiple series including Back of the Pack and Sippin' Series.

Experience a scenic cross country trail run through Wilderness Run Vineyards featuring a 5K and 1 Mile distance. Enjoy post race live music and refreshments at the winery to support St. Patrick School.

A 5k cross country run and 1 mile fun run through Ruppert Nurseries' 500 acre tree farm in Gaithersburg on March 22, 2026. Proceeds support the Montgomery County Children’s Opportunity Alliance.

This 41-mile mountain trail race loops through the George Washington National Forest, featuring waterfalls, cliffs, and 8,000 feet of climbing. With a strict field limit and remote course, crews are not permitted. Top finishers earn cash pr..

Experience a timed trail ultra at Little Bennett Regional Park with 5 hour and 9 hour challenges for solo runners and relay teams. Complete as many 4.4 mile loops as possible and enjoy a post race chili bar.

Trek across the rugged western slope of Massanutten in Virginia. Choose a distance from 7 to 28 miles, with the option to carry weight for an extra challenge. Finish within 10 hours on a course of single-track, fire roads, and ridgeline tra..

Experience a classic 50 mile trail run through Virginia's spring beauty. The course winds through rolling forested terrain along the Occoquan River and Bull Run, featuring large bluebell stands. This event, with its historic Civil War theme..

Run a scenic 5k cross-country course at a Virginia vineyard. The event welcomes runners and walkers alike and offers virtual participation options. It takes place in Warrenton on April 4, 2026.

The Trail Demon 10k is a technical trail race on a forest loop at Dirt Farm Brewing in Virginia. Runners receive a finisher medal, a tech shirt, and a post race beer. Proceeds support the Boulder Crest Foundation for veterans and first resp..

Trail races of 5K and 10K take place at ThorpeWood private property in Thurmont, Maryland on April 4, 2026. Both are part of the FSRC Grand Prix, chip timed, with marked loops, on-site water and designated parking.

UltraTrax Wisp brings a timed trail adventure to Wisp Resort on April 11, 2026. Choose from four loop-based distances up to 28 miles, with stunning Appalachian views and a festive after-party. Finishers earn rewards, and part of the proceed..