Trail Running calendar near Winchester 2026-2027

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 team-based 5k at Burke Lake Park that raises funds for programs serving people with intellectual and developmental disabilities. The event also offers a family friendly 2k fun walk, chip timing, and team and age group awards.

A night trail event in Prince William Forest Park offering 50 mile, 25 mile, and 10 mile races on a 25 plus mile loop with staffed aid stations at Telegraph Road Pavilion and Oak Ridge Camp Ground.

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 rocky out and back trail race near Frederick, MD offering 50K and 25K on shaded singletrack with stream crossings, three aid stations and mandatory on course hydration for a self reliant trail experience.

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.

A 12 hour trail event in Berkeley Springs WV on a scenic, technical five mile single track loop with about 750 feet of elevation change per loop. Aid stations, a post race meal, and handcrafted awards are part of the event.

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.

A just under 50 km trail run in the southern Massanutten range with about 5,700 ft of elevation change, six aid stations, and a start and finish at the Route 211 parking area. Entry is limited to 75 runners.

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.

Experience the twisty single track and scenic farm fields of Germantown at this trail running event. Participants can choose between two distances while supporting local non profits in Montgomery County.

Experience a scenic run or walk along the Chesapeake and Ohio Canal path in Georgetown for the Christmas in July 5k and Half. Participants can choose between two race distances or join virtually from any location.

Experience the ridges and valleys of Pennsylvania with point to point and loop races through Blue Knob State Park. Choose between 50k, half marathon, or 10k distances on technical single track and mountain trails.