Trail Running calendar near Winchester 2026-2027

Experience an evening run through the historic Manassas National Battlefield with the Night Raider 5k and 10k. Finish your race at The Winery at Bull Run and enjoy a post-race gathering at this scenic Virginia vineyard.

Run or walk a scenic off road 5K course along the Cacapon River and Lewis Farm. This benefit event supports local youth programs while celebrating the Wardensville Spring Fest with local food and creativity.

Test your endurance at Furbutt’s Backyard 24 Hour where runners complete a 4.167 mile loop ogni hour on a scenic trail course. Whether you aim for 24 hours or the nighttime 12 hour option, this event focuses on community and persistence.

Experience a downhill 3 km run through the scenic quartzite ridges of Seneca Rocks. This free gravel road event crosses the Potomac River as part of the Fourest Festival celebrations.

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.

The Last One Standing Challenge tests endurance with a unique backyard format. Runners must complete a 4.167-mile or 1-mile loop every hour until only one remains. It's a qualifier for the Backyard Ultra world championship, with prize money..

Test your endurance at Operation CENTURION on the Rock Creek Trail near Washington D.C. Complete ten 10 mile loops for a total of 100 miles within a 32 hour time limit.

Experience a scenic loop course through Sky Meadows State Park featuring views of fields and streams. This event offers 5k and 10k distances for both runners and walkers in the heart of Delaplane.

Experience the FXBG Trail 5 Miler at Motts Run Reservoir in Fredericksburg. This five mile trail race features three distinct climbs and over 300 feet of elevation gain along a scenic and flowing course.

Tackle the historic Old Dominion 100, a classic ultramarathon loop through Virginia's Massanutten Mountains. The challenging course mixes roads and trails with 14,000 feet of climbing. Earn a silver buckle by finishing within 24 hours in th..

This 45th annual memorial race honors coach Gary Brown with a fast, flat five-mile out-and-back on the shaded C&O Canal Towpath. Participants receive chip timing, a tech shirt, and awards. A student entry option is available for this Willia..

Experience a low key trail event at Colonel Denning State Park featuring significant elevation gain and scenic vistas. Choose between two distances that provide a relaxed atmosphere and a community focused post race celebration.

Run through history on the secret training trails of the CIA's predecessor in Prince William Forest Park. This night event features a 50-mile, two-loop course with a 14.5-hour limit, or a single 25-mile option. Pacers are allowed for the se..

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..

Celebrate Juneteenth with a scenic trail run through the hilly terrain of Schaeffer Farm in Germantown. Choose between 6k and 12k distances on a course that welcomes both runners and walkers.

Experience an ultra marathon through the Monongahela National Forest and Dolly Sods Wilderness Areas. Run across various terrains including boulder filled plains and ancient sphagnum bogs in the mountains of West Virginia.

Event Overview The Catoctin 50k Trail Run takes place in June. It offers two distances: a 50k (approximately 32 miles) and a 25k called the "Half Cat." The event is held in Cunningham Falls State Park and Gambrill State Park near..

Experience a scenic run or walk along the Chesapeake and Ohio Canal path in the heart of Georgetown. Choose between a 5k or 10k course located right near the nations capital.

Experience the scenic beauty of West Virginia at the Canaan Valley Trail Run. Choose between 5.9 and 11.8 mile distances on the Promised Land Trail with post race snacks and finisher medals provided.

Kick off the Blue Crab Bolt series at Seneca Creek State Park with scenic 5K and 10K trail runs featuring lake views and singletrack paths. Enjoy professional race support, post-run breakfast burritos, and a festive atmosphere.