Trail Running calendar near Winchester 2026-2027

A backyard ultra at Manidokan Camp in Knoxville, MD on May 30, 2026, featuring official 4.167 mile laps and a 1 mile 24 hour event. On-site camping, aid station, showers, timing, shirts, and cash prizes for the winner and the assist.

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.

Trail run and walk on May 30, 2026 at Gentle Giants Draft Horse Rescue in Mt. Airy, MD featuring 1 mile and 5K courses across forest trails and open pasture with draft horses on the farm.

A loop course at Sky Meadows State Park on May 31, 2026 offering 5K and 10K distances plus virtual options. The route passes fields, streams and sometimes cows, and walkers are welcome.

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.

A measured 100 miles loop through the Massanutten Mountains and Shenandoah River Valley featuring 14 climbs and about 14,000 feet of gain. The mixed road and trail course has a 24 hour cutoff to earn the silver buckle.

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.

A trail ultramarathon in Prince William Forest Park offering 50, 25, and 10 mile options on a 25+ mile loop with staffed aid stations and historical OSS/CIA park setting.

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.

A rugged out-and-back trail event near Frederick, MD offering a 50K and a 25K Half Cat, shaded forest and stream crossings, staffed aid stations, capped fields, and a mandatory water requirement for all runners.

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.

Trail race on the Promised Land Trail behind Canaan Valley Resort offering a one-loop 5.9 mile and a two-loop 11.8 mile option. The field is limited to 200 participants and entrants receive a T-shirt and finisher medal.

A trail running event at Seneca Creek State Park on June 27, 2026, offering measured 5K and 10K courses through singletrack with lake views, aid stations, post-race food, and age division awards.

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 free Forrest Gump themed fun run on Lakeside Loop in Owings Mills offering a full 4.4 mile loop or a 1 mile out-and-back option, meeting at New Town Village Center with themed attire suggested.

Experience the West Side Quarry trail race along the Rappahannock River in Fredericksburg. This 10k course features a steady climb and rolling hills with 426 feet of elevation gain for a dynamic running experience.

Experience a scenic run through the 868 Estate Vineyards in Purcellville. Choose between 5k and 10k distances or participate virtually for an afternoon of outdoor activity at a Virginia vineyard.