Trail Running calendar near Winchester 2026-2027

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.

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.

The Tommy Laudani Delone Dash 5K Trail Run will take place in Hanover on Saturday 1 August 2026. You can run 5 kilometers.

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.

A remote trail event on routes near the Wild Oak Trail, held on a roughly 60 km course with a 50 km party option. The route has about 8,000 feet of climbing, limited aid stations, minimal course markings, and a restricted field size.

Join this annual memorial event in Schellsburg for a 5K run or walk through scenic rolling hills or a family friendly flat course. Support local scholarships while competing for age group awards and cash prizes.

All trail race at Patapsco Pickall Area offering 25K and 50K on rolling single track with technical sections and river crossings. Aid stations provide water Tailwind and real food and the finish includes shelter food and beer.

The Gettysburg Brewfest Trail 5K will take place in Gettysburg on Saturday 15 August 2026. You can run 5 kilometers.

Experience the MCRRC Groovin Woodstock 7K XC at the Woodstock Equestrian Center in Maryland. This low key cross country race offers a scenic 7 km route for club members and non members alike.

Experience the Leopold’s Preserve 5k and 10k in Broad Run Virginia. This Sippin Series event welcomes both runners and walkers for a scenic race through the preserve in collaboration with the Farm Brewery at Broad Run.

Experience an engaging 8 mile trail race through the winding singletrack of Fredericksburg. Navigate rolling hills and punchy climbs in this focused event supported by the local running community.

Conquer rugged terrain and steep inclines at Dirt Farm Brewing in Bluemont. Choose between 5k and 10k distances through breathtaking landscapes and enjoy a post race beer at the finish line.

An out-and-back 3.8 mile run at Pen Mar Park with about 1.8 miles of ascent to High Rock Overlook. Held August 30, 2026, with registration deadlines and a higher fee on race day.

Experience a cross country race through Nottoway Park followed by a community picnic. This event features a three mile course and a kids fun run to celebrate the end of the summer season.

A 71-mile, orange-blazed circuit on the Massanutten Trail with rugged, rocky terrain, multiple aid stations and two drop bag options, strict qualification and entry limits, and enforced cutoffs.