Trail Running calendar near McGaheysville 2026-2027

Experience the scenic and historical landscape of Winchester Virginia with a 5k, 10k, or Half Marathon at Third Winchester Battlefield. Both runners and walkers are welcome to participate in person or virtually.

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.

A 3.1 miles obstacle course through Thomas Jefferson’s Poplar Forest with elite, team, corporate and non-competitive waves. Entry fees support Poplar Forest education and elite competitors must complete all obstacles to qualify for prizes.

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.

Experience a cross-country run through the scenic grounds of Albemarle CiderWorks in Virginia. Choose between 5k and 10k distances or participate virtually followed by post-race cider at the orchard.

Run through the beautiful Fifty-Third Winery & Vineyard in Louisa, Virginia. This 5k and 10k event supports animal rescue and sanctuary efforts for local wildlife and farm animals.

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.

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.

Experience the mountain trails of Douthat State Park with four race distances ranging from six miles to a 50K ultra. Runners will navigate waterfalls and climbing sections within the scenic Virginia State Park Adventure Series.

A multi-distance trail running festival in the Shenandoah Valley offering 100M, 100K, 50K and 21K races on technical mountain terrain with UTMB World Series and Western States qualification.

Woodstock Warrior is a looped trail event at Seven Bends State Park near Woodstock, VA offering 10 mile, 50k, 50 mile, 100 mile and Last Man Standing Ruck distances on mixed terrain. Each loop is about 10 miles with roughly 1600 ft of gain.

Trail event at Powhatan State Park with 10 mile and 5 mile running and hiking options along the James River. Part proceeds benefit the Friends of Powhatan State Park and a water station and post-event food sales are provided.

Join the 7th annual Trails 4 Miles for a fall challenge at Sherando Park. Choose from a mixed-surface 4-mile trail run, a new mountain bike time trial, or a one-mile fun run/walk. All proceeds support the I'm Just Me Movement.

A 33.3 mile single-loop trail run in the George Washington National Forest with 6150 feet of elevation change. The route includes three aid stations and a climb to Big Schloss with broad 360° ridge and valley views.

Experience the full reservoir trail system on this thirteen mile course in Fredericksburg. Runners navigate flowing singletrack and five distinct climbs totaling over nine hundred feet of elevation gain through scenic wooded terrain.

A 110 mile trail ultramarathon in the Massanutten range with 22,300 feet of elevation gain, a 48 hour limit, required second half crew support, and limited course markings and medical services.

Experience a technical trail race with your dog at a scenic equine rehabilitation facility in Virginia. Enjoy distances from 1.25 miles to 10K followed by a finishers festival with food trucks and a biergarten.

Experience a flat and fast race through West Virginia at the Greenbrier River Trail Marathon. This scenic event offers full and half marathon distances within the beautiful Cass Scenic Railroad State Park.