Trail Running calendar near Chesapeake 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 two mile timed dune run and a one mile Color Fun Run take place at Jockey's Ridge State Park on July 3, 2026. Proceeds support Friends of Jockey's Ridge and the event includes awards and a post race gathering.

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.

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.

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.

Test your endurance at Jockey High Ridge State Park by completing a 5k loop every hour for five hours. Run the full 25k solo or pair up with a teammate to tackle this unique coastal loop challenge.

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.

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.

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.

A 24 hour ultrarun on the Roanoke Canal Trail using an out and back *10k* loop with start and finish at Weldon Mills Distillery on the Roanoke River. Held December 5 to 6, 2026; registration opens August 1, fee $120.

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.