Trail Running calendar near Winchester 2026-2027

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 road and trail event at Third Winchester Battlefield in Winchester VA on August 8 2026 offering 5K, 10K, half marathon and virtual options. Walkers are welcome.

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 5K and 10K held at Bull Run Marina in Clifton, VA on August 15, 2026, with in-person and virtual entry options and variable 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.

Leopold’s Preserve 5k & 10k in Broad Run, VA on August 23, 2026 features 5 km and 10 km distances, welcomes walkers, and offers virtual entry options with medal and shirt choices.

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 race at Dirt Farm Brewing in Bluemont VA offering 5 km and 10 km routes plus virtual options. The courses run on rugged, winding trails with steep climbs and descents through rural landscapes.

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.

Trails 4 Tails at Codorus State Park offers a 40 mile ultra, a team relay and a 25K on a looped trail course that mixes pavement, fields, singletrack and shoreline, with aid stations, camping and a race day picnic nearby.