Trail Running calendar near Yorktown 2026-2027

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.

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..

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 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.

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 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.

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.

A scenic 5K along the Virginia Capital Trail in Rocketts Landing, Richmond, on October 31, 2026. The event offers an in person 5K plus virtual entry options with medal and shirt choices.

Virginia Beast 2026 is a multi-day rucking event in Virginia Beach on 6 to 8 November 2026. Events vary in distance and competitors must be prepared to carry 40 lb, 50 lb, or 80 lb rucks.

Experience the only race held on the scenic Noland Trail in Newport News. Runners can tackle the 50 km distance solo or as a relay team while enjoying a post race festival with live music and tastings.

A free Thanksgiving community event at Pocahontas State Park featuring a cross-country 5K and a short kids fun run. Registration is required; the day includes alumni photos, raffle drawings, and optional donations for a memorial award suppo..

A set of timed trail events at Windsor Castle Park in Smithfield VA offering 8 hour and 4 hour formats, a 10K, and ruck categories. Laps are counted, aid station is stocked with hot items, and all finishers receive a homemade medal.

Multiple USATF certified races take place on the Dismal Swamp course in Chesapeake, VA, including 50K, marathon, half marathon and a 50K relay. Aid stations are provided and finishers receive apparel and medals.

Races of 5K, 10K and half marathon take place on December 12, 2026 at Pocahontas State Park in Chesterfield, VA. Courses run through the wooded Bright Hope Trail area and walkers are welcome.