Trail Running calendar near Chesterfield 2026-2027

A half marathon and a 50K on the Dahlgren Railroad Heritage Trail in King George, VA on August 8, 2026. Mostly flat rails to trails courses with time limits, finisher medals, apparel options and postrace food including free MooThru ice crea..

A 12 hour endurance run at Oak Grove Lake Park in Chesapeake VA on repeated 1.5 mile loops. The tree lined, unpaved course circles the lake, has one aid station, and is limited to 60 runners.

Experience an engaging 8 mile trail race through the winding singletrack of Fredericksburg. Navigate rolling hills and punchy climbs in this focused event supported by the local running community.

A cross country 5 km and 10 km at Albemarle CiderWorks in North Garden, VA on August 30, 2026, offering in person and virtual entries plus post race cider.

Annual running event at Fifty-Third Winery & Vineyard in Louisa VA offering 5 km and 10 km races plus virtual options to benefit 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.

A community running event in Farmville on September 12, 2026 offering in-person and virtual 5K and 10K races plus hand cycle divisions on a flat, crushed gravel out-and-back course along the High Bridge State Park Trail.

A 5K running race hosted by Hartwood High School Cross Country on September 12, 2026 in Stafford, VA. It is the first annual StallionsXC Open and serves as the opening race of the Stallion Invitational, with high school races afterward.

Join the community at Newport News Park for a 5k run across grass, gravel, and paved trails. This accessible local event offers a varied multi surface course through the scenic park grounds.

A stadium climb at Virginia Credit Union Stadium on September 13 honoring those lost on September 11 and supporting first responders and military. Climbers ascend sections 1 to 23 five times, with a wheelchair accessible concourse route ava..

Trail runs of 10 and 5 miles at Powhatan State Park during the Pawpaw festival, featuring riverside singletrack, open-field views, a water station near mile 5, festival amenities, and park lodging options.

A trail 5K along the historic Roanoke Canal and a Half Mile Fun Walk in Roanoke Rapids, with proceeds helping replace historic batteau replicas and age-group awards for finishers.

Run the Rock | Rockville is the fourth annual 5K at Luck Stone’s Rockville quarry near Richmond, featuring gravel terrain, quarry views, local food vendors, family activities, swag, and raffles supporting a charitable cause.

A four-mile cross-country style trail race around Beaver Lake at Pocahontas State Park on September 26, 2026, featuring fire roads, single-track with short technical sections, cupless hydration, and a $25 registration fee.

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.

AUSA Southern Virginia Chapter hosts a timed 3rd Annual 5K and 10K on the Virginia Capital Trail in Charles City, with race timing, a finisher medal, event SWAG, and proceeds supporting the Charles City High School JROTC Scholarship Fund.

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.

A canicross and trail event on October 3, 2026 in Gordonsville, VA offering competitive 10K and 5K races, a 1.25 mile sprint, a casual dog friendly 5K, and a virtual 5K, with technical trails, three water stations, and a Finisher's Festival..

An outdoor adventure race in Midlothian, VA on October 3, 2026 where participants use a map to find 5 to 7 hidden control points and collect tokens. First three finishers with all tokens are champions and a portion of proceeds supports Semp..