Trail Running calendar near Woodstock 2026-2027

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.

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..

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.

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..

Trail 5K and 10K at Seneca Creek State Park in Gaithersburg, MD featuring singletrack trails, lake views, aid stations, post race food, and a charity partner Interfaith Works.

This cross-country event takes place at the Agricultural History Farm Park in Derwood, Maryland. It's part of a free series for members, with paid registration available for non-members and a youth discount.

A cross country 5k and 10k at 868 Estate Vineyards with chip timing, a virtual option, race awards, and a postrace glass of wine for participants.

Trail race at Button Farm Living History Center in Germantown on July 25, 2026, offering 5K and 10K courses on maintained single track with stream crossings and some rocky, rooty sections.

Run a festive half marathon or 5K on the scenic C&O Canal path in Georgetown. The event benefits the Purple Heart Foundation and counts towards year-long running series points. Participants receive a medal, tech shirt, and chip timing.

Trail races at Little Bennett Regional Park on August 1, 2026 offer 5K and 10K singletrack courses with hills, stream-side sections, aid stations and post race food.