Trail Running calendar near Chesapeake 2025-2026

The Virginia Run for Cancer is a unique running event scheduled for April 26, 2025, in Hampton, VA. Participants can choose to compete individually or as part of a team in a 24-hour race format. The event aims to raise funds for the American Cancer Society, with a lifetime total of $310,000 raised t..

The Taskinas Creek Half Marathon, taking place at York River State Park in Williamsburg, VA, is a scenic and challenging race set for June 1, 2025. This event features a course primarily composed of trail surfaces, including single track and dirt fire roads, with a small section of pavement. Partici..

The Night Owl 9K is an exciting running event taking place at Freedom Park in Williamsburg, VA. This challenging race features a mix of single track, fire road, and paved trails, with rolling hills and technical sections. Participants can enjoy a post-race party with beer and pizza, and all finisher..

The Terrible Twelve is a unique 12-hour running event taking place in Williamsburg, VA, where participants can walk or run on a scenic 3.7-mile loop trail. This self-supported race encourages camaraderie, as runners are required to volunteer for an hour during the event, helping fellow participants..

The One Mile With a Smile 12 Hour Endurance Run is a flexible race held at Oak Grove Lake Park in Chesapeake, VA. Participants can run as much or as little as they wish within a 12-hour period, completing laps on a 1.5-mile unpaved, flat loop that offers scenic views of the lake, forest, and wildlif..

The Pocahontas Trail Festival is a running event taking place at Pocahontas State Park in Chesterfield, Virginia. Scheduled for October 5, 2025, the festival features a Half Marathon and a 10k race, both designed to showcase the park's scenic trails. Participants will enjoy professionally timed race..

The Another Round 25K is an inaugural running event scheduled for October 18, 2025, at Jockey's Ridge State Park in Nags Head, North Carolina. Participants will complete five 5K loops, with the challenge of finishing one loop every hour between 7:30 a.m. and 12:30 p.m.The race caters to endurance an..

The Greensprings 24 is a 24-hour endurance race held in Williamsburg, VA, starting on October 25, 2025. Participants can run, walk, or crawl on a scenic, flat, crushed gravel loop course, with each loop measuring 2.215 miles. The event encourages runners to reach personal milestones such as 50 miles..

Haunts & Hallows is a half marathon event organized by Winding Way Run Co., taking place in the scenic trails of First Landing State Park, Virginia Beach. This inclusive event welcomes runners of all levels, offering a supportive community atmosphere. Participants can enjoy a beautiful course featur..

The Noland Trail 50K and Relay is a unique running event taking place in Newport News, VA, on November 1, 2025. Participants can choose to compete in a solo 50K or as part of a relay team consisting of 2-6 members. The course features six laps on the scenic Noland Trail within The Mariners’ Museum P..

The Pocahontas Half is a scenic race held at Pocahontas State Park near Richmond, featuring a half-marathon course along the wooded Bright Hope Trail. The event also includes 5k and 10k races, with courses that are primarily forest trails composed of dirt and pine needles, offering a softer running..

The Mel Williams Memorial Seashore 50K, presented by Brooks, is a trail running event taking place at First Landing State Park in Virginia Beach. This challenging race features a two-loop course, with participants passing through two fully stocked aid stations multiple times. Runners will receive a..

The Snowy Owl 10 Mile is a trail race set in the scenic York River State Park, featuring a challenging course that includes five miles of technical single track, dirt fire roads, and a variety of terrain with an elevation gain of approximately 600 feet. Participants can expect rocky sections, twisti..

The Swammie Shuffle 200 is a charitable ultramarathon held in Virginia Beach, VA, to raise awareness and funds for veteran mental health and suicide prevention. Participants run over 200 miles along the coast, starting at Sandbridge Beach and passing through the Outer Banks of North Carolina, with n..