Trail Running calendar near Chesapeake 2026-2027

A 5K run and walk at Appomattox River Regional Park in N. Prince George on April 11, 2026. All participants receive a medal and awards will recognize top overall and age group finishers; early registrants receive T shirts while sizes last.

Test your endurance at Mount Trashmore with this unique weight based loop event. Complete 4.8 mile circuits where the weight increases with every loop until only one remains.

A coastal trail ultrarun in First Landing State Park, Virginia Beach, with a 60k (two loops) and 30k (one loop) across nine named trails, varied coastal habitats, a ten hour cutoff and three staffed aid stations with a provided collapsible..

Celebrate the 40th anniversary of this historic charity race through the Nags Head Woods Ecological Preserve. Run a 5K on gravel roads or enjoy a 1 mile walk to support local community initiatives in the Outer Banks.

Experience cross country racing at Bells Mill Park with 5K and 1.5 mile events featuring grass and marshy terrain. Enjoy a post race afterparty with catered lunch boxes and finisher medals for all participants.

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.

Experience summer trail running on the dirt paths of Sandy Bottom Nature Park. This three race series offers increasing distances from 5k to 5 miles to support local scholarship funds.

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.

Conquer the iconic sand dunes at Jockey's Ridge State Park in this unique 2-mile run/walk. Your effort supports the preservation of the park. All finishers earn a medal and can celebrate at the post-race party.

A 10 hour loop event at Windsor Castle Park in Smithfield VA on a 3.1 mile trail with about 150 ft gain per loop. Event options include 10 hour, 5 hour, 2 hour and a one lap 5k and rucking is allowed.

Muddy Princess Virginia Beach is a women only 5k obstacle mud run at Historic Greenbrier Farms. Join a community focused on empowerment and fun while supporting the fight against breast cancer.

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 24 hour endurance race at Greensprings in Williamsburg on October 24, 2026. Runners complete certified 2.215 mile loops on a mainly flat crushed gravel trail while supporting The Arc in Williamsburg.

A trail half marathon at First Landing State Park with roots, bridges, sandy sections and about 300 feet of elevation gain. The event includes four aid stations, shirts and finisher beanies, and supports AIDNOW.

A 50K trail race at The Mariners' Museum Park in Newport News offering a solo 50K and relay teams of two to six, run as six laps on the Noland Trail with access to the Mariners' Museum Fall Festival.

Get Outside 8 Hour at Windsor Castle Park in Smithfield, VA is a chip timed loop event on a 5 km course offering 8 hour and 4 hour formats, a 10K, and ruck options. A stocked aid station will serve hot items and all finishers receive a hand..

A set of in-person races on December 12, 2026 at Pocahontas State Park near Chesterfield VA offering 5K, 10K and a half marathon through the Bright Hope Trail area; walkers are welcome and virtual options are available.

Experience a two loop trail ultramarathon through the scenic First Landing State Park in Virginia Beach. Enjoy a supported 50 km course followed by a post race celebration with pizza and refreshments.

A half marathon and a 5K at Harwoods Mill Park in Yorktown on January 17, 2026, with shuttle parking from McReynolds Athletic Complex. Limited fields, four aid stations, on-site packet pick-up and specific trail conditions.