Trail Running calendar near Woodstock 2026-2027

The Paradise Springs 5k & 10k is a running event at Hemlock Overlook in Clifton, Virginia. Participants can choose from the 5k or 10k course, with a post race celebration at Paradise Springs Winery. The event takes place on February 28, 202..

On March 1, 2026 at Wakefield Park in Annandale, the Spring Backyard Burn offers 5.5 mile and 10 mile trail race options across singletrack, doubletrack, stream crossings and minimal pavement. The event features aid stations, post race food..

A women only trail endurance event near Triangle VA offering 50K and 25K options, two roughly 15 mile loops, five aid stations, and a limited field with a 9 hour cut off.

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..

Trail marathon and 50K on March 7, 2026 at Seneca Creek State Park near Gaithersburg, MD. Runners may stop at the marathon finish or continue to complete the 50K, and entries include a tech shirt and finisher medal.

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..

Run a 25K or 10K on the private trails of Panorama Farms in Virginia. The course is mostly wooded single and doubletrack with views of Naked Creek and the Blue Ridge Mountains. This event supports the local running community and is Trail Si..

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.

Bel Monte Endurance Races in Lyndhurst, Virginia offer 50 Miler, 50K and 25K trail courses through the George Washington National Forest with substantial elevation gain. Entries are non-refundable.

A trail race at the Workhouse Arts Center in Lorton on March 15, 2026, offering mostly singletrack through forest and meadows with options of roughly 5.4 miles or 10 miles. The event includes aid stations, optional medals, a kids program, a..

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.

A trail event at Wilderness Run Vineyards in Locust Grove featuring a 5K and a 1 Mile run, on-site parking, post race music and food, drink tickets for runners over 21, and proceeds benefiting St Patrick School.

A cross-country 5K and 1 Mile run at Wilderness Run Vineyards in Spotsylvania on March 21, 2026, featuring trail hills, on-site parking, a food truck and live music, drink tickets for adults, a 50/50 raffle, and awards across multiple age g..

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.

A 41.4 mile trail ultra in Virginia's Shenandoah Valley featuring about 8,000 feet of climb, six fully stocked aid stations, notable natural landmarks, and a 125 runner field limit. Crews and pacers are not allowed.

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..

A 50 mile trail run near Clifton, Virginia that follows forested, rolling terrain along Bull Run and the Occoquan River. The 2026 race is the 32nd running and features large bluebell stands and a 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..