Trail Running calendar near Chesterfield 2026-2027

Multi-hour trail event at Windsor Castle Park in Smithfield, VA featuring a 3.1 mile loop with about 150 ft gain per lap. Options include 10 hour, 5 hour, 2 hour and a one-lap 5k, with a rucking option and on-course aid station.

A lakeside trail race at Boar's Head Resort in Charlottesville on July 11, 2026, featuring a 5.2 mile loop with about 745 feet of elevation change. The race is open to runners and walkers and is part of the Summer Trail Running Series.

Experience the West Side Quarry trail race along the Rappahannock River in Fredericksburg. This 10k course features a steady climb and rolling hills with 426 feet of elevation gain for a dynamic running experience.

Muddy Dash Richmond on July 25, 2026 at Virginia Motorsports Park is a non-competitive 5K with obstacles, mud pits, and on-site Pre-Party and After-Party festivities. Family-friendly registration options include value and VIP packages.

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 with repeated laps of a 1.5 mile unpaved, tree-lined loop and one aid station. The field is limited to 60 runners and registration closes July 25.

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 family friendly 5K mud run at Budds Creek Motocross Park on August 29, 2026, featuring obstacles, mud pits, slides, a Pre Party and an After Party with music and food. Standard and VIP registration options are available.

A 5 km and 10 km running event at Albemarle CiderWorks in North Garden, VA on August 30, 2026, with a cross-country course introduced for 2025 and both in-person and virtual entry options including medal and shirt choices.

The 53rd Winery 5K and 10K on September 5, 2026 takes place at Fifty-Third Winery & Vineyard in Louisa, Virginia. The event includes 5K, 10K and virtual options and benefits 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.