Trail Running calendar near Williamsburg 2026-2027

A half marathon and a 50K on the Dahlgren Railroad Heritage Trail in King George, VA on August 8, 2026. Mostly flat rails to trails courses with time limits, finisher medals, apparel options and postrace food including free MooThru ice crea..

A 12 hour endurance run at Oak Grove Lake Park in Chesapeake VA on repeated 1.5 mile loops. The tree lined, unpaved course circles the lake, has one aid station, and is limited to 60 runners.

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.

Join the community at Newport News Park for a 5k run across grass, gravel, and paved trails. This accessible local event offers a varied multi surface course through the scenic park grounds.

Trail runs of 10 and 5 miles at Powhatan State Park during the Pawpaw festival, featuring riverside singletrack, open-field views, a water station near mile 5, festival amenities, and park lodging options.

A trail 5K along the historic Roanoke Canal and a Half Mile Fun Walk in Roanoke Rapids, with proceeds helping replace historic batteau replicas and age-group awards for finishers.

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 four-mile cross-country style trail race around Beaver Lake at Pocahontas State Park on September 26, 2026, featuring fire roads, single-track with short technical sections, cupless hydration, and a $25 registration fee.

AUSA Southern Virginia Chapter hosts a timed 3rd Annual 5K and 10K on the Virginia Capital Trail in Charles City, with race timing, a finisher medal, event SWAG, and proceeds supporting the Charles City High School JROTC Scholarship Fund.

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.

An outdoor adventure race in Midlothian, VA on October 3, 2026 where participants use a map to find 5 to 7 hidden control points and collect tokens. First three finishers with all tokens are champions and a portion of proceeds supports Semp..

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.

First annual 4 miles trail run and hike at York River State Park on October 10, 2026. Dirt trails include single track and gravel, the format is non competitive, all finishers receive medals and leashed dogs are allowed.

Hog Jog in Smithfield on October 10, 2026 features an in-person 5K through Windsor Castle Park, a Piglet Kids Run, and a Virtual 5K with medals and T shirt included.

An eight-hour loop event at Powhatan State Park on an approximately 2.7-mile field-and-forest loop, with a Parent Loop for families, one aid station at the trailhead, and options for solo or four-person relay entries.

Run Wild Races stages biannual runs and an obstacle course at the Metro Richmond Zoo, with net proceeds benefiting Pygmy Sloth conservation. Participants get free zoo admission and spectators a 10% discount.

A 24-hour loop endurance race in Williamsburg, VA on certified 2.215-mile loops, with distance awards, on-site support, team tracking, and proceeds benefiting The Arc in Williamsburg.

A trail half marathon at First Landing State Park with sandy sections, roots, bridges, and about 300 feet of elevation gain; includes event shirt, finisher beanie, donuts, and age-group awards.

Halloween-themed 5k and 10k at Indian Fields Tavern/5 Fields Brewing Co. with costume judging, official timing, finisher medal and a finish-line beer.

A 5k along the Virginia Capital Trail in Rocketts Landing, VA on October 31, 2026 with in-person and multiple virtual entry options.