Trail Running calendar near Stephens City 2026-2027

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.

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 runners take on the scenic and challenging courses of Fountainhead Regional Park. Distances include a half marathon and a 10K, featuring the Bull Run Occoquan Trail and notable hills. The event also hosts the Collegiate Running Associ..

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.

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.

Join the Ed Poling Memorial HARC Hike for Hunger & Hope, now in its 14th year. Choose from scenic C&O Canal Towpath hikes in May or a challenging Appalachian Trail hike. This fundraising event supports local community programs.

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..

Join the 14th annual Hike for Hunger & Hope with two events. Choose a challenging 10 or 20-mile Appalachian Trail hike in May or a scenic 5K/10K on the C&O Canal. All hikes support local food programs and refugee services.

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.

The Old Dominion is a classic 100-mile loop through Virginia's Massanutten Mountains and Shenandoah River Valley. With 14,000 feet of climbing over mixed terrain, it tests endurance against a 24-hour clock. It's a key event in the Grand Sla..

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.

The Highlands Sky 40 Mile Trail Run explores the rugged highlands of West Virginia. Runners traverse the Roaring Plains and Dolly Sods Wilderness in the Monongahela National Forest. The scenic course finishes at Canaan Valley State Park.

A rugged out and back on the Catoctin Blue Trail near Frederick, MD offering a 50K and a 25K Half Cat, with rocky singletrack, shaded forest, stream crossings, three staffed aid stations, and mandatory carried hydration.

Run the scenic Puso 10K on the flat, gravel C&O Canal path in Georgetown, Washington DC. This chip-timed event benefits the PUSO Foundation and awards top finishers. All participants receive a finisher's medal and tech shirt.

The Canaan Valley Trail Run takes place on the scenic Promised Land Trail loop in West Virginia's state park. Choose a 5.9-mile or 11.8-mile distance and receive a medal, shirt, and post-race refreshments. Experience the natural beauty of T..