Trail Running calendar near Keswick 2026-2027

A road race at Fifty-Third Winery in Louisa, Virginia on September 5, 2026 offering 5K, 10K and several virtual options, with proceeds benefiting Hooves & Paws Animal Rescue.

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.

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.

Run a scenic off road trail through a 1000 acre farm bordering the Rappahannock River. Enjoy a post race celebration at the brewery with live music craft beer and a souvenir pint glass.

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.

A looped trail event at Seven Bends State Park offering 10-mile loops with mixed terrain and multiple distances from 10 miles to 100 miles, plus a Last Man Standing Ruck; timed cutoffs and specific pacer and drop rules apply.

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.

Trails 4 Miles is an annual event at Sherando Park with a mixed-surface four mile trail race, an untimed one mile fun run on the paved path, and a new mountain bike time trial. Proceeds support the I'm Just Me Movement.

A 33.3 mile single loop trail run in the George Washington National Forest featuring a climb of Big Schloss with 360 degree views and three aid stations. Entry is limited to 60 runners and opens August 3, 2026.

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 miles trail ultramarathon in the Massanutten range with 22,300 feet of climbing and a 48 hours limit. The reverse MMT route uses rugged singletrack, includes two climbs of Waterfall, and requires crew support for the second half.

Trail canicross races at Caledon State Park offer two distances, allow leashed dogs, and provide a reusable speedCup; entry fees support Friends of Caledon State Park.

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.

An 18th annual 12 hour trail event at Prince William Forest Park near Triangle, VA, run on a 6.5 mile figure eight loop. Field limited to 100 runners; two aid stations and a post race meal are provided.

Experience the scenic beauty of Pocahontas State Park at this trail festival featuring a loop course 10k and half marathon. Enjoy runnable trails and professional timing in a picturesque Virginia forest setting.

Trail races at the Workhouse Arts Center in Lorton VA on October 4, 2026. Options of 5.4 or 10 miles on mostly singletrack through forest and meadow across the former prison grounds.

A fall trail event at Pohick Bay Regional Park offering 5 km and 10 km race options plus virtual entries; walkers are welcome and multiple registration tiers are available.

Three consecutive trail runs on the Eastern Continental Divide take place in the Monongahela National Forest over Columbus Day Weekend. Distances are 50 kilometers, 50 miles and a 13.1 mile run near Spruce Knob and Seneca Rocks.

A trail endurance event at Powhatan State Park centered on a 2.7 mile loop with about 60 feet of elevation per lap. Multiple formats include an eight hour individual, a four person relay, an eight hour hiker and a timed Parent Loop.