Trail Running calendar near Winchester 2026-2027

Locust Shade 5k & 10k on July 25, 2026 at Locust Shade Park in Triangle VA offers shaded, scenic trail courses plus virtual options with medals and shirts. Walkers are welcome.

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.

Scenic road and trail races at Third Winchester Battlefield in Winchester VA on August 8, 2026, offering 5K, 10K and a half marathon plus virtual entry options with medal or shirt. Walkers are welcome and registration runs in phased windows..

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 memorial trail run in the Jefferson National Forest featuring a roughly 60 km course and a 50 km Party Route option, three aid stations, limited entry, and a largely unmarked route supported by a GPX file and turnsheet.

A 5K run plus two 5K walks on August 9 2026 at Camp Living Water in Schellsburg PA, raising funds for annual scholarships for Bedford High School students and for families facing financial need after the loss of a young person.

Trail running at Patapsco Pickall Area with 25K and 50K options on rolling single track, river crossings, mandatory out-and-backs, staffed aid stations with real food, and a postrace gathering with food and beer.

A trail 5K in Gettysburg on August 15, 2026, with a race shirt option for early registrants and an event bottle opener medal. Brewfest options and tours of the Daniel Lady Farm House and Barn are available the same day.

A running event on August 15, 2026 at Bull Run Marina in Clifton VA, offering in-person 5K and 10K races plus multiple virtual entry options with varying merchandise choices and tiered registration fees.

A 7K trail race at the Woodstock Equestrian Center with a hilly course that circles fields and runs through wooded single track, presented as a 1969 throwback with 60s music and period attire encouraged.

A 5K and 10K event at Leopold’s Preserve in Broad Run on August 23, 2026, offering in-person and virtual options and included in the Sippin Series 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.

Trail-style 5K and 10K at Dirt Farm Brewing in Bluemont, VA on August 29, 2026, featuring rugged terrain, steep climbs, and virtual entry options with medals and shirts.

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 clockwise 71-mile circuit of the orange-blazed Massanutten Trail around Fort Valley, VA, with 13,500 ft of elevation change, scheduled aid stations, strict qualifications and enforced cut-offs; GPX and aid charts are provided.

A 10 mile trail race in Fredericksburg, VA that follows the Rappahannock River, moves through rolling hills, and finishes with a sustained climb. Top three men and top three women receive gift certificates.

Mountain trail event on Blue Knob near Claysburg offering 10K, half-marathon and 50K courses with significant elevation and technical rocky terrain. Aid stations, a swag package, and post race food and beer are provided.

Tails on Trails 5K Run/Walk is the second annual 3.1 miles run, walk, and virtual event at Cacapon State Park on September 12, 2026. The wooded cross country course passes the upper lake and ends with awards and a free pup swim.