Trail Running calendar near Williamsburg 2026-2027

A three-race summer trail series at Sandy Bottom Nature Park organized by the Peninsula Track Club, featuring 5K, 4-mile, and 5-mile events plus a full-series entry and awards across age groups and walker categories.

A mud-run fundraiser in King George, VA on June 27, 2026, featuring a 4-mile obstacle course and a 1-mile kids run, organized by the Dahlgren Lions Club with team awards by group size.

Night Owl 9k at Freedom Park in Williamsburg VA is a night trail race over single track, fire road and paved trails with rolling hills and technical sections. Post race activities include pizza, beer and wildlife education.

A 10 hour trail event at Windsor Castle Park in Smithfield, VA on a 3.1 mile loop with about 150 ft gain per lap. Shorter 5 hour, 2 hour and one lap 5k options are offered along with rucking divisions and an aid station.

Muddy Princess Virginia Beach is a 5K obstacle mud run at Historic Greenbrier Farms on July 19, 2026. The event offers Standard, VIP and volunteer options, finishers medals and digital photos, and supports the National Breast Cancer Foundat..

Family friendly 5K mud run at Virginia Motorsports Park in Richmond with obstacles, waist deep mud pits, a pre party and an after party with music and food. Standard and VIP registration options are available.

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 with repeated laps of a 1.5 mile tree lined unpaved loop and lake views. The field is limited to 60 runners and one aid station is available.

A family-friendly 5K mud run on August 29, 2026 at Budds Creek Motocross Park featuring obstacles, mud pits, a pre event warm up, and an after party with music and food. Value and VIP registration options are available.

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.

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.

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.

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 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.

A Halloween themed 4 mile trail run and hike at York River State Park on October 10, 2026. The new trail features single track, river views and rolling hills, with finisher medals for all and a two hour time limit.

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 October 24, 2026, run on a USATF certified 2.215 mile crushed gravel course. Individual and team mileage are tracked, awards are given for multiple distances, and proceeds support The Arc..

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.