Virginia
Virginia Trail Running Calendar 2026-2027
Explore the best trail runs in Virginia for 2026-2027! Our updated list features 161 exciting trail runs across the region. Find your next trail run in Virginia below and join the trail community at these great events!
September 2026
A 13.6 mile loop race starting and finishing at High Knob Observation Tower in Wise County, held Sunday September 20, 2026. The course runs mainly on Forest Service roads and proceeds support trail development in the Flag Rock and High Knob areas.
Scenic 5 km and 10 km at Burke Lake Park on September 20 with chip timing, tech shirt, medal, virtual option, and proceeds benefiting Operation Turbo.
Run through the Flag Rock Area Trails in Norton Virginia during a unique festival celebrating local folklore and the mythical Woodbooger creature.
Trail event at Sherando Park in Stephens City, VA offering a timed 4-mile mixed-surface race and an untimed 1-mile out-and-back on the paved path, supporting I'm Just Me Movement.
Run the Rock | Rockville is the fourth annual 5K at Luck Stone’s Rockville quarry near Richmond, featuring gravel terrain, quarry views, local food vendors, family activities, swag, and raffles supporting a charitable cause.
A 4 mile cross country trail race around Beaver Lake at Pocahontas State Park on Sept 26, 2026, held with Chesterfield Outdoor Fest; cupless with awards and on-site demos.
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.
October 2026
A 110-mile Massanutten trail ultramarathon with 22,300 feet of elevation, a 48-hour limit, required second half crew support, limited course markings, and no medical coverage on course.
The second annual Breast Run Ever is a community 5K at the Virginia Beach Sportsplex on October 2, 2026, with pink race shirts, finisher medals, and all profits donated to the Pink Fund.
A timed loop running festival in Damascus Town Park offering 3 hour, 6 hour and 12 hour races on a scenic one mile loop, with camping for registered runners, live music, food trucks, aid stations, and awards.
Experience an uphill 10K race climbing over 2,000 feet from downtown Norton to the highest point of the Cumberland Mountains at High Knob.
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.
Trail 5K, 10K and half marathon at Burke Lake Park on October 3 with chip timing, finisher medal, water stations and a virtual race option.
A canicross and trail event on October 3, 2026 in Gordonsville, VA offering competitive 10K and 5K races, a 1.25 mile sprint, a casual dog friendly 5K, and a virtual 5K, with technical trails, three water stations, and a Finisher's Festival.
Test your endurance on a 6.5 mile trail loop at Prince William Forest Park with individual and relay options focused on completing the most mileage in 12 hours.
A chip timed 5k trail race at Claude Moore Park on October 3 with a medal, cotton shirt, virtual option, and series points for multiple season standings.
An open-course adventure race in Midlothian where participants use a map to find 5 to 7 checkpoints, earn tokens, and support Semper Fi & Americas Fund.
Community trail run in Potomac Shores on October 3, 2026 featuring 5K and 10K courses on wooded trails, free of charge.
Multi-distance charity walk, run and relay in Quantico on Oct 3 and 4 2026 supporting Semper Fi & America's Fund with individual and team 24 hour options.
A community day at John Paul the Great Montessori Academy featuring a 2 mile obstacle trail run, a 2 mile no obstacles run, a 1 mile kids obstacle and family activities.