Trail Running calendar near Williamsburg 2026-2027

A mostly trail, low frills half marathon at York River State Park on June 7 2026 with a new Hike a Half option, marked trails, aid stations, and a five hour time limit.

A June 2026 backyard ultra in Midlothian, Virginia using repeated 4.167 mile loops each hour until one runner remains. An Ultra Mini option lets participants choose how many loops to run and all entrants receive a commemorative shirt.

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.

Trail-based multi-hour event at Windsor Castle Park in Smithfield, VA with 10 hour, 5 hour, 2 hour and one-lap 5k options on a 3.1 mile loop that gains about 150 ft per circuit.

A women only 5K obstacle mud run with 18+ obstacles at Historic Greenbrier Farms in Chesapeake, VA on July 19, 2026. Open to participants aged 7 and up, the event welcomes running, jogging or walking and emphasizes teamwork and fun.

The Muddy Dash - Richmond, VA will take place in Matoaca on Saturday 25 July 2026.

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, made of repeated laps of a 1.5 mile loop. The unpaved, tree lined course features lake and forest views and is limited to 60 runners.

Muddy Dash Maryland is a mud obstacle event at Budds Creek Motocross Park on August 29, 2026 offering Value and VIP registrations, packet pickup the day before, free spectator admission, and a program donating registrations to local communi..

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 and hikes at Powhatan State Park along the James River with 10 and 5 mile options, a water station near mile 5, early-registration shirts, and proceeds benefiting the Friends of Powhatan State Park.

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.

An eight hour looped trail event at Powhatan State Park featuring a 2.7 mile loop and about 60 feet of elevation change per lap. Options include individual, relay, hiker, and a Parent Loop for family laps.

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. Runs use a certified 2.215 mile crushed gravel loop with distance awards and proceeds benefiting The Arc.