Trail Running calendar near Massanutten 2026-2027

Run through the scenic vineyards of Barrel Oak Winery on a challenging cross-country course with hills and gravel paths. Runners receive a finisher's medal, tech shirt, and a glass of wine, with proceeds supporting veterans. A virtual optio..

Run a scenic loop course on the light gravel trails of Third Winchester Battlefield. Choose from 5k, 10k, or half marathon distances, with chip timing, medals, and shirts for all participants. Points count towards annual series, and walkers..

This 5k offers a scenic cross-country loop around the Bluemont Station Brewery & Winery property. Runners receive a technical shirt, finisher medal, and a post-race beverage. The event supports the I AM ALS charity and features a virtual pa..

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.

Perfect Day 50K in Massanutten is a 50 kilometer event on May 2, 2026, at Massanutten Western Slope near Keezletown, Virginia. It offers individual entries and team options for two or three people with a listed price of $99 per person.

Freight Train Ultra Marathon in Farmville, VA offers 100k, 50k and a half marathon on a relatively flat rail trail that crosses High Bridge twice. The event includes aid stations, drop bag support at Prospect and a 19 hour limit for the 100..

A 100 mile trail ultramarathon in the Massanutten Mountains with rocky terrain, short steep climbs totaling over 18,000 feet of ascent and a 36 hour cutoff. The event features well stocked aid stations, marked trails and lodging options.

A May trail festival in Snowshoe, West Virginia offering races from a kids mile to a 100K ultramarathon. The weekend pairs trail running with historic railroad rides, local markets, live music, and family activities in Snowshoe Village.

Race through history on the trails of Manassas National Battlefield at dusk. The Night Raider offers 5k and 10k distances starting and finishing at the Winery at Bull Run. Runners receive a medal, tech shirt, and a post race glass of wine.

West Virginia Trail Fest is a family friendly trail running festival each May around Snowshoe in Pocahontas County, with scenic forest and single track races for all ages. Enjoy kids activities, a historic train ride and community fun.

Join a scenic 5K run/walk beside the Cacapon River in Wardensville, West Virginia. The event is part of the town's Spring Fest and all proceeds support local youth programs. Run, walk, or cheer before enjoying a day of community celebration..

Event Details The Memorial Day 10K Run & 2 Mile Walk takes place on Monday, May 25, 2026, in Lynchburg, Virginia. It is organized by the Community Access Network (CAN) and is the seventh race in the 2026 Lynchburg Road Runners Race Seri..

Run a scenic but technical loop trail at Sky Meadows. The event features a 5k and 10k, with finisher medals and chip timing. Points count towards multiple race series, and walkers are welcome.

A measured *100-mile* loop through the Massanutten Mountains and Shenandoah River Valley with varied terrain, 14,000 feet of gain and 14 climbs. The volunteer-run event offers a 24 hour cutoff for the silver buckle.

A night-focused trail event at Prince William Forest Park offering a 50 mile race plus 25 mile and 10 mile options. The 50 mile uses a 25+ mile loop run twice and features staffed aid stations and specific crew and pacer rules.

Event Overview The Fauquier Education Farm 5K and Fun Run is a fundraising event for the Fauquier Education Farm, a 501(c)(3) organization. The organization's mission is to advance agriculture through education and best practice farming. It..

A 40 mile trail run in Canaan Valley, West Virginia, held in mid June and routed mainly through Monongahela National Forest. The course crosses Dolly Sods and Roaring Plains with a mix of plateau, bogs, forest paths, and rocky plains.

A night trail event on High Bridge Trail State Park near Farmville VA offering 50K, half marathon and 5K options including hiker and family entries. The course follows an old rail trail with aid stations, chip timing and a cupless policy.

The High Bridge Challenge pairs the Freight Train and Night Train on High Bridge Trail in Farmville, VA. Runners can combine distances across four combo options and receive a special handcrafted award for completing both races.

A trail race on the Promised Land Trail in Canaan Valley State Park on June 27 2026, offering one-loop and two-loop options. Participants receive a finisher medal, a McClumsy T shirt, post race snacks and beer for those 21 and older.