Trail Running calendar near Chesterfield 2026-2027

We have found 34 Trailruns within 80 miles of Chesterfield. See below where and when you can find the races.

The Naked Creek Trail Race offers 25K and 10K courses on the private, scenic trails of Panorama Farms in Virginia. Runners can experience wooded singletrack with views of the reservoir and Blue Ridge Mountains. The event provides a unique c..

Event Details The Dogwood Ultra Marathons are held every March at Twin Lakes State Park in Green Bay, Virginia. The event offers several formats: a 10 Mile race, 12 Hour, 24 Hour, and 48 Hour solo runs, and relay options for each time domai..

Run a scenic cross-country trail through Wilderness Run Vineyards. This event on March 21, 2026, features a 5K and a 1 Mile run, with post-race food, music, and a drink for participants over 21. Proceeds benefit St. Patrick School.

A 5K trail event at Chanco on the James in Surry County offering run, walk, and hike options along woods and the James River; online registration closes March 19 and race day registration is available.

Experience a scenic cross country trail run through Wilderness Run Vineyards featuring a 5K and 1 Mile distance. Enjoy post race live music and refreshments at the winery to support St. Patrick School.

Event Details The Women's Trail Festival is a two-day event at Freedom Park in Williamsburg, VA, scheduled for a Saturday and Sunday in late March. The event features trail running and hiking options over two distances. Distances and Format..

April 2026

Run a memorable 14-mile point-to-point trail adventure from one Sheetz to another. This untimed event features themed aid stations with unique snacks, supports local charities, and provides useful swag like an insulated travel mug.

Run a scenic loop course along the James River in April. Choose your target distance from 10 miles to 50 miles, with a unique format that credits you as a finisher for any distance you complete. The event offers aid stations, pacers on long..

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.

Run a scenic, four-lap cross-country 10k at Southern Revere Cellars. Your registration includes chip timing, a tech shirt, and a post-race beverage. The event supports a local animal rescue charity.

Choose from three scenic vineyard runs at Delfosse Winery. Tackle challenging summits for rewarding views across the 3k, 6k, or 9k courses. Virtual participation options are also available.

Run Fest at Panorama Farms offers a day of trail racing and community celebration on April 18, 2026. Choose from a 4-mile trail race, a team relay, or a 1-mile fun run, followed by a festival with live music and local food. It's a chance to..

Four teams of eight runners will complete a 122.4 mile relay at Pocahontas State Park on April 24 and 25, 2026, with proceeds supporting Kids On The Move, a Sports Backers youth running program.

May 2026

Event Overview The Freight Train Ultra Marathon is a multi-distance trail running event held at High Bridge Trail State Park. It offers a half marathon, 50k, and 100k distance. The event takes place in early May. Course Details All races st..

Event Overview The Trail Running Events at Dominion Energy Riverrock is a series of trail races taking place over three days in May. All events start and finish at the Belle Isle Parking Lot in Richmond, Virginia. The Races Three separate t..

Run for a cause on the scenic Virginia Capital Trail at the Motion for Justice 5K. This flat, paved course offers views of the James River and includes chip timing, a finisher medal, and a tech shirt. Awards recognize top overall and age gr..

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.

June 2026

Celebrate National Trails Day on a flat, scenic 5k course across the historic High Bridge. This event welcomes runners and walkers, with all proceeds supporting park programs. Every participant gets a hat, finishers earn a medal, and local..

Event Format The Taskinas Creek Half Marathon for 2026 is described as a "no frills" or "Hike-a-Half" event. The organizer's stated goal is to be inclusive rather than competitive, with the aim of keeping entry fees low...

Run under the stars on an historic rail trail at High Bridge Trail State Park. Choose from a 50K, half marathon, or 5K, with hiker-friendly and new family options available. Prepare for a hot, cupless race where carrying water is mandatory.