Trail Running calendar near Chesterfield County 2026-2027

A 5k and 10k cross-country run at Albemarle CiderWorks on August 30, 2026, with virtual participation options. The course is new for 2025 and cider will be available after the event.

A road race at Fifty-Third Winery in Louisa, Virginia on September 5, 2026 offering 5K, 10K and several virtual options, with proceeds benefiting Hooves & Paws Animal Rescue.

A 10 mile trail race in Fredericksburg, VA that follows the Rappahannock River, moves through rolling hills, and finishes with a sustained climb. Top three men and top three women receive gift certificates.

Run a scenic off road trail through a 1000 acre farm bordering the Rappahannock River. Enjoy a post race celebration at the brewery with live music craft beer and a souvenir pint glass.

Trail runs and hikes at Powhatan State Park along the James River with 10 and 5 mile options, a water station near mile 5, early-registration shirts, and proceeds benefiting the Friends of Powhatan State Park.

Run the Rock Rockville is the fourth annual 5K at Luck Stone Rockville on 26 September 2026, featuring a course through a working quarry and a post race zone with vendors, music, raffles, and family activities.

Experience the full reservoir trail system on this thirteen mile course in Fredericksburg. Runners navigate flowing singletrack and five distinct climbs totaling over nine hundred feet of elevation gain through scenic wooded terrain.

Trail canicross races at Caledon State Park offer two distances, allow leashed dogs, and provide a reusable speedCup; entry fees support Friends of Caledon State Park.

Experience a technical trail race with your dog at a scenic equine rehabilitation facility in Virginia. Enjoy distances from 1.25 miles to 10K followed by a finishers festival with food trucks and a biergarten.

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.

A Halloween themed 4 mile trail run and hike at York River State Park on a new course that includes dirt trails, rolling hills, single track and riverside views. The format is non competitive with finisher medals and post race refreshments.

Run scenic looped trails at Medoc Mountain State Park with single track, varied hills and a summit loop in 5 and 10 mile options. Limited to 500 runners, the race offers shirts, unique medals and hearty postrace soup and hot dogs.

An eight hour looped trail event at Powhatan State Park featuring a 2.7 mile loop and about 60 feet of elevation change per lap. Options include individual, relay, hiker, and a Parent Loop for family laps.

Andy's Backyard Ultra is a last person standing ultra at Teventrails in Earlysville, VA where runners complete a 4.17 mile loop each hour. The final finisher is the runner who completes one more lap than all other entrants.

Greensprings 24 is a 24 hour loop endurance race in Williamsburg, VA on October 24, 2026. The USATF certified course, multiple distance awards, team tracking, and proceeds benefiting The Arc make it a timed endurance event.

A community fundraising trail event at Crozet Park offering a 5K, a limited 10K with a creek crossing, and a 0.75-mile family run. The day includes T-shirts, a pancake breakfast, a post-race festival, live music and proceeds for local trail..

A 50K race on the Noland Trail at Mariners' Museum Park in Newport News on November 7, 2026, offered as a solo 50K or as relay teams of two to six, with festival access included.

Trail races at Walnut Creek Park on November 8, 2026 offering 5K and 10K distances plus virtual entries with medal and shirt options. Registration fees vary by entry type and by registration date.

A free Thanksgiving community event at Pocahontas State Park featuring a cross-country 5K and a short kids fun run. Registration is required; the day includes alumni photos, raffle drawings, and optional donations for a memorial award suppo..

A post-Thanksgiving running event at Lake Anna State Park on November 27, 2026, offering a trail 5K, 10K and half marathon with mixed trail and road surfaces, plus virtual options that include medal or shirt choices.