Trail Running calendar near Chesterfield 2026-2027

A mid February trail event at Holiday Lake near Appomattox offering 50K, 25K and a mostly single track 10K. Loop courses use trails and country roads with aid stations about every four miles.

A cross country 5k and 10k at Wilderness Run and 1781 Brewing in Spotsylvania on February 14, with on-course water stations, chip timing, finisher awards, a virtual option, and proceeds benefiting Semper Fi and America’s Fund.

A trail running weekend at Bear Creek Lake State Park in Cumberland, VA, featuring a 10 mile loop, a 4.2 mile mini on park trails and single track, and a virtual 10 mile option. In-person fields are limited and some awards are age specific.

Trail races near Leonardtown, MD on an ~10.5 mile loop around a 250 acre lake, offered as 17K, 34K, or 50K with two aid stations and a 100 runner limit.

Run a 25K or 10K on the private trails of Panorama Farms in Virginia. The course is mostly wooded single and doubletrack with views of Naked Creek and the Blue Ridge Mountains. This event supports the local running community and is Trail Si..

A loop course at Twin Lakes State Park with multiple timed options from a 10 Mile to 48 Hour solo or relay, single aid station with hot food and gluten free choices, plus primitive camping and a Parent Loop 5k.

A trail event at Wilderness Run Vineyards in Locust Grove featuring a 5K and a 1 Mile run, on-site parking, post race music and food, drink tickets for runners over 21, and proceeds benefiting 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.

A cross-country 5K and 1 Mile run at Wilderness Run Vineyards in Spotsylvania on March 21, 2026, featuring trail hills, on-site parking, a food truck and live music, drink tickets for adults, a 50/50 raffle, and awards across multiple age g..

A two-day women's trail festival in Williamsburg, VA with a competitive ten mile trail run plus an 8k and noncompetitive hikes, talks, and exercise classes. Proceeds support local charities and all finishers receive a medal and a T shirt.

A 14-mile untimed point to point trail run in King George, Virginia following the Dahlgren Railroad Heritage Trail. The cupless event features themed aid stations, shuttle service, practical finish swag and supports Sheetz For the Kidz.

A looped trail event at James River State Park offering 10 mile, 50k, 50 mile and relay options, with varied singletrack and riverside flats and a loop-based finish system.

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.

A hilly 3k 6k and 9k loop around Mountain and Vine Vineyards with chip timing, a finisher medal and a glass of wine. Points count toward several yearlong series and the event supports the local volunteer fire department.

A new spring trail running festival at Panorama Farms offers a 4-mile race, a 4-person relay, and a family-friendly 1-mile run. An after-party with local food, beer, and music follows, with drink proceeds supporting a local school program.

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.

Freight Train Ultra Marathon in Farmville, VA offers 100k, 50k and a half marathon on a relatively flat rail trail that crosses High Bridge twice. The event includes aid stations, drop bag support at Prospect and a 19 hour limit for the 100..

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..

On May 16, 2026 at Bells Mill Park in Chesapeake the Strider XC Classic features a 5K cross country race, a competitive 5K race walk, and a 1.5 mile kids race, with one aid station, shirts for the first 150 registrants, and medals for all f..