Trail Running calendar near Winchester 2026-2027

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.

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 Johnnycake Jolt Series is a four-week trail run event on Wednesday evenings in May. Runners can tackle a scenic 10 km course in the Pickall Area of Patapsco Valley State Park. It’s a grassroots series designed to bring the local running..

A multi distance trail event in Waterford VA on May 9, 2026 that runs through historic village streets, vineyards, trails and unpaved roads. Proceeds support the Waterford Foundation and 5K and 10K finishers receive a shirt and medal.

The Johnnycake Jolt Series offers four weekly 10k trail runs in Patapsco Valley State Park. It's a grassroots, low-key event organized by park stewards, with a discount for park members.

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 spring road-and-trail event at Carderock Recreation Area with 5k, 10k and half-marathon out-and-back routes on the C&O Canal towpath, chip timing, finisher's coin, technical shirt, water stations, and a virtual option.

Supported hikes on the C&O Canal and the Appalachian Trail raise funds for Micah's Backpack and the Refugee Welcome Network. Options include 5K, 10K and longer challenge distances with route support and a post hike lunch.

The Johnnycake Jolt Series offers four weekly 10k trail runs in Patapsco Valley State Park. It's a grassroots, low-key event organized by park stewards, with a discount for park members.

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.

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..

The Johnnycake Jolt Series offers four weekly 10k trail runs in Patapsco Valley State Park. It's a grassroots, low-key event organized by park stewards, with a discount for park members.

A May fundraising series on the C&O Canal and Appalachian Trail supporting HARC programs, with distances from 5K to a 20-mile challenge, on-trail support, and a post-hike celebration lunch.

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 45th annual five-mile out-and-back on the C&O Canal Towpath in Williamsport, MD, on June 6, 2026. Chip timing, a technical race shirt, and age-group and overall awards are part of the event.

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 trail race on June 19 at Button Farm in Germantown offering 6k and 12k distances around the Schaeffer Farm Trails. The event counts toward series scoring, includes chip timing, shirts and medals, and offers a virtual option.

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.