Trail Running calendar near Winchester 2026-2027

A 40 mile trail run in Davis, West Virginia on June 20th, 2026 that crosses Monongahela National Forest and Dolly Sods. The 22nd edition covers plateau terrain, bogs, woodland paths, and rocky plains.

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 road running event on July 11, 2026 at Nottoway Park in Vienna, VA offering 5K and 10K in-person races plus virtual options with tiered registration fees and medal and shirt choices.

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.

A vineyard run at 868 Estate Vineyards in Purcellville, VA on July 25, 2026 offering 5k and 10k routes plus virtual entry options and tiered registration fees.

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.

A community trail event on July 25, 2026 at Locust Shade Park in Triangle VA offering 5K and 10K races plus virtual entries with medal or shirt options. Walkers are welcome and entry fees vary by registration period.

Trail races at Little Bennett Regional Park on August 1, 2026 feature a 3.7 mile 5K plus and a 6.2 mile 10K on twisty singletrack with hills and streamside sections. Staging is near the Prescott Horse Trailer Area in Clarksburg Maryland.

Trail races of 5K and 3K at Codorus State Park Marina organized by Delone Catholic High School's cross country team; early registration includes a T-shirt and goodie bag and proceeds support several local funds.

A race day at Third Winchester Battlefield on August 8, 2026 offering 5K, 10K, and half marathon distances plus virtual options and tiered registration fees; walkers are welcome and courses pass through battlefield scenery.

Participate in a 5K run or walk at the Somerset Historical Center to support the North Star Cross Country team. Enjoy a dedicated cross country course with awards for various age groups and included event t-shirts.