Trail Running calendar near Williamsburg 2025-2026

The Night Owl 9K is a challenging trail race held at Freedom Park in Williamsburg, Virginia. The 9-kilometer course features a mix of single track, fire road, and paved trails with rolling hills and technical sections including roots and twists, ideal for runners familiar with mountain bike-style tr..

The DHRT 50K is an exciting trail running event set in King George, Virginia, taking place on August 2, 2025. This challenging race traverses the scenic Dahlgren Railroad Heritage Trail, offering participants a flat and well-maintained course primarily shaded by trees. Runners will face the added ch..

The 3H Trail Half Marathon in King George, Virginia, is a scenic, flat, and fast out-and-back race held entirely on the Dahlgren Railroad Heritage Trail, a converted railroad bed offering solid footing with surfaces of dirt, gravel, grass, and pine needles. The course starts at the eastern end of th..

The Dahlgren Heritage Rail Trail 50K is a challenging ultramarathon held annually in King George, Virginia, with the 2025 race scheduled for August 2. The course is a flat, fast, and mostly shaded out-and-back route along the Dahlgren Railroad Heritage Trail, a converted railroad bed featuring dirt,..

The Terrible Twelve is a 12-hour self-supported trail running event held at the Warhill Nature Trail in Williamsburg, Virginia. Participants run or walk as many 3.7-mile loops as possible on a crushed gravel course featuring rolling hills and scenic views, though personal lighting is required for ni..

The One Mile With a Smile 12 Hour Endurance Run takes place at Oak Grove Lake Park in Chesapeake, Virginia. Participants run multiple laps of a 1.5-mile loop over 12 hours, allowing runners to cover as much or as little distance as they choose. The course is flat, unpaved, and tree-lined, offering s..

The Pawpaw 10 Miler and 5 Miler take place at Powhatan State Park in Powhatan, Virginia, featuring scenic runs along the James River, through open fields, shaded forests, and past historic cabin ruins. The event offers a 10-mile race and a shorter 5-mile option, both incorporating diverse terrain in..

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 Piedmont 8 Hour is an annual trail running event held at Powhatan State Park in Powhatan, Virginia. Celebrating its 10th year, the race features a 2.7-mile loop with about 60 feet of elevation change, winding through open meadows and pine forests with scenic fall foliage. The course is mostly ru..

The Greensprings 24 is a 24-hour endurance race held in Williamsburg, VA, benefiting The Arc of Greater Williamsburg, a nonprofit supporting adults with developmental disabilities. The race features a USATF-certified 2.215-mile loop course on mainly flat, scenic, crushed gravel trails with minimal e..

The Smithfield Hog Jog is an annual 5K run and walk held at Windsor Castle Park in Smithfield, Virginia. The event features a 5K race with chip timing and a Kid's Piglet Run, where all young participants receive awards. The race welcomes up to 500 participants and offers awards across various age gr..

Haunts & Hallows is a half marathon trail race held in Virginia Beach, VA, at First Landing State Park. The course features gently rolling trails with about 300 feet of elevation gain, including roots, bridges, and sandy sections, offering scenic and varied terrain. The event fosters a supportive co..

The Noland Trail 50K & Relay is a unique running event held in Newport News, Virginia, within The Mariners’ Museum Park. Participants can choose to run the solo 50K or join a relay team of 2 to 6 members, collectively completing six laps on the scenic Noland Trail, with short course sections before..

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 challenging trail race held at York River State Park in Williamsburg, Virginia. The course features a mix of terrain including five miles of technical single track trails, about three-quarters of a mile on road, and the remainder on dirt fire road trails. Runners will enco..

The Dahlgren Trail Half Marathon is a scenic running event taking place on the Dahlgren Railroad Heritage Trail in King George, Virginia. This half marathon features a flat, out-and-back course that showcases the natural beauty of the area. Participants can enjoy cash prizes, custom finisher medals,..

The Swammie Shuffle 200 is an ultramarathon held in Virginia Beach, VA, covering over 200 miles. Runners start at Sandbridge Beach and head south through the Outer Banks of North Carolina to the Cape Hatteras Lighthouse, the turnaround point, before returning to the start. The course features scenic..

Blackbeard’s Revenge 100 is an ultra-distance running event held on North Carolina’s Outer Banks, spanning from Corolla to Hatteras. Scheduled for March 21-22, 2026, the race offers 100-mile and 100K solo distances, as well as a 100-mile relay option for teams. The course is entirely paved and featu..

The Sheetz-to-Sheetz Trail Run is a 14-mile untimed point-to-point trail run held in King George, Virginia. Starting at a Sheetz convenience store near King George Middle School, the course follows rural roads briefly before transitioning to the flat, well-marked Dahlgren Railroad Heritage Trail, a..