Trail Running calendar near Woodstock 2026-2027

Run among saplings and open fields in the Breeze Thru The Trees 5K or enjoy a relaxed 1 mile fun run on Ruppert Nurseries' scenic tree farm in Gaithersburg. Proceeds benefit the Montgomery County Children's Opportunity Alliance to expand ea..

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.

A 50 mile trail run in early April that follows trails near the Occoquan River and Bull Run in Clifton, Virginia, passing large bluebell stands and noting local Civil War sites. The 2026 race is the 32nd running.

Enjoy a scenic three loop 5k through Molon Lave Winery in Warrenton on April 4, 2026. Walkers and virtual runners welcome and finishers receive a winery glass, medal and tech shirt for a festive post race celebration.

Join the Trail Demon 5k and 10k at Dirt Farm Brewing in Bluemont, VA on April 4, 2026, with in person or virtual entries. Expect technical forest trails, a finisher medal, tech shirt, chip timing and a post race beer.

UltraTrax Wisp at Wisp Resort on April 11, 2026 offers 7, 14, 21, and 28 mile loop options across singletrack and ski trails, optional 10/20/35 lb rucks, a 10-hour finish window, and finisher gear including a patch and shirt.

Run through scenic vineyard trails at Southern Revere Cellars on April 18, 2026 with 5k and 10k options and a virtual race. Enjoy a postrace glass of wine or beer while supporting Hooves & Paws Animal Rescue.

Run scenic vineyard loops at Mountain & Vine in Faber with 3k, 6k or 9k over hilly terrain. Enjoy a finisher medal, tech shirt and a glass of wine while supporting the Nelson County volunteer fire department.

Run Fest at Panorama Farms is an inaugural spring trail festival on private farm trails near Charlottesville with a 4 mile, a family 1 mile and a 4 person relay. Enjoy an after party with local beer, food and music while supporting the UVA..

Run 3k or 6k through Barrel Oak Winery vineyards in Delaplane VA on April 19, 2026 for a rolling cross country experience. Enjoy a glass of wine, a medal and tech shirt while supporting Semper Fi and America's Fund; virtual and pet friendly..

A trail race at Lake Fairfax Park in Reston on April 19, 2026 offering 5.1 mile and 10 mile singletrack courses with short technical sections and lake views. Aid stations, post race food, optional finisher medals, and a kids program are ava..

Join Spring Hops on April 19 at Red Shedman Brewery for a scenic 5K through hop fields and vineyards. Mixed terrain, great views and a celebratory pour for every finisher make this a fun spring run for runners and beer lovers alike.

A 100 mile ultramarathon on the C&O Canal towpath near the Potomac River. The course is one 40 mile loop plus two 30 mile loops with multiple aid stations and low elevation terrain. WSER 2027 qualifier.

Run the scenic Third Winchester Battlefield on April 25 with 5K, 10K and half marathon options plus a virtual race. Enjoy chip timing, a finisher medal and tech shirt while supporting Team Virginia and organ transplant awareness.

Run three scenic laps around Bluemont Station Brewery & Winery in Bluemont, VA on April 26, 2026, and enjoy chip timing, a finisher medal, shirt, and a complimentary beer or wine. Walkers and virtual runners welcome.

A 5K trail run and walk on private property near Amissville, Virginia, benefiting the Chefs For Kids Foundation. The mostly dirt course has gentle hills; registration includes a race T-shirt, bib, and post-race refreshments.

A timed trail event at Agricultural History Farm Park in Derwood, Maryland on May 2, 2026. Runners repeat a 5 mile out and back lap under one hour for 3, 6, or 10 hours; a marathon and 25K are also offered.

The Perfect Day 50K will take place in Keezletown on Saturday 2 May 2026. You can run 50 kilometers.

Trail races at Fountainhead Regional Park include an 11ish km 10K course and a 13.5 mile half marathon with multiple aid stations offering water and Gatorade. The event includes virtual options and supports the charity Homestretch.

The Historic Waterford Trail Run/Walk will take place in Waterford on Saturday 9 May 2026. You can run between 5 and 10 kilometers.