Trail Running calendar near Chesterfield 2026-2027

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 mixed-surface trail race with single track, fire road and paved sections, rolling hills and technical terrain. Walkers are welcome and all finishers receive medals.

A community trail run organized by Logic Fitness Club starting from Wharf Hill Brewing Company in Smithfield, VA. The route is roughly 3.0 miles on gravel and dirt with about 127 ft of elevation gain and lasts about one hour.

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.

A lakeside trail race at Boar's Head Resort in Charlottesville on July 11, 2026, featuring a 5.2 mile loop with about 745 feet of elevation change. The race is open to runners and walkers and is part of the Summer Trail Running Series.

Experience the West Side Quarry trail race along the Rappahannock River in Fredericksburg. This 10k course features a steady climb and rolling hills with 426 feet of elevation gain for a dynamic running experience.

Muddy Dash Richmond on July 25, 2026 at Virginia Motorsports Park is a non-competitive 5K with obstacles, mud pits, and on-site Pre-Party and After-Party festivities. Family-friendly registration options include value and VIP packages.

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.

Experience an engaging 8 mile trail race through the winding singletrack of Fredericksburg. Navigate rolling hills and punchy climbs in this focused event supported by the local running community.

A family friendly 5K mud run at Budds Creek Motocross Park on August 29, 2026, featuring obstacles, mud pits, slides, a Pre Party and an After Party with music and food. Standard and VIP registration options are available.

A new course at Albemarle CiderWorks on August 30, 2026 features in-person 5 km and 10 km races plus virtual entries; the route uses cross-country terrain and cider is available at the venue after the event.

A community running event at Fifty-Third Winery & Vineyard in Louisa, VA on September 5, 2026, with 5 km and 10 km courses plus virtual options. Proceeds support Hooves & Paws Animal Rescue and its sanctuary work.

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.

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.

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.

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.

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..