Trail Running calendar near Chesterfield 2025-2026

Wine & Country Run is a true cross-country 5K fundraiser held at the Hampton Roads Vineyard & Winery in Elberon, Virginia. The scenic, 3.1-mile course winds through Virginia’s countryside for an open-category race with awards for the top male and female finishers (plus masters divisions) and a kids..

The Orchard Dash is a cross‑country trail race at Albemarle CiderWorks in North Garden, Virginia. Runners choose between 5k (two laps) and 10k (four laps) on a hilly, wooded course that differs from the winter route. The event blends competition with a festive atmosphere: finishers receive a glass o..

The Roanoke Canal 5k is a trail race in Roanoke Rapids, North Carolina, along the historic Roanoke Canal built in 1823. It offers a 5K and a 1/2 Mile Fun Walk, with proceeds supporting the Roanoke Canal Museum’s batteau exhibit. The course runs on the Roanoke Canal Trail—a natural-surface, generally..

The Hare and Tortoise 8K/5K Run Walk, 1 Mile Fun Run is a fundraising race in Williamsburg, Virginia along the Capital Trail. The event offers 8K Run/Walk, 8K Competitive Walk, 5K Run/Walk, 8K/5K Virtual options, and a 1-Mile Fun Run. Courses are USATF certified.Participants receive a swag bag, cust..

Pawpaw 10 Miler and 5 Miler take place at Powhatan State Park in Powhatan, Virginia, pairing a park-centered trail race with the Pawpaw Festival. The events offer a 10-mile main course and a 5-mile option (plus hiker variants) that wind along the James River: riverfront flats, open fields, and shady..

9K for Semper K9 is a community running and walking event in Fredericksburg, Virginia, held at Old Mill Park along Canal Path by the Rappahannock River. The program includes a 9K race and a Kids .9 Mile Fun Run, welcoming runners, walkers, families. The course runs along canal paths in downtown Fred..

Run the Vineyards - Wind Vineyards 5K is a scenic trail race held at Wind Vineyards, 5178 Richmond Highway, Tappahannock, Virginia. The 5K route runs on well-groomed, hard-packed dirt and grassy trails across the 200-acre property, with two short hills and mostly flat sections. The event features ch..

Run to the Taproom - Creekside Farm Brewery 5K & 8K takes place at Creekside Farm Brewery in King George, Virginia. The event offers scenic 5K and 8K courses on a well-maintained dirt trail through a 1,000-acre farm bordering the Rappahannock River. It is chip-timed with awards for Top 3 Overall and..

The Fox Trot 5k in Keswick is a scenic cross-country race held at Merrie Mill Farm & Vineyard. The event features a 5k course that includes a mix of flat gravel, dirt, paved roads, and some notable hills, offering a varied terrain for runners. Participants also have the option to run a 1-mile distan..

Association of the United States Army Southern Virginia 5K, held in Charles City, Virginia, uses the scenic Capital Trail for its two-distance event. Now in its second year, the race offers a 5K Run/Walk and a 10K Run/Walk along the Capital Trail, open to all paces. Registration includes an official..

Howlin' Coyote Canicross Trail Race, held in King George, Virginia (11617 Caledon Rd), offers two canicross options: a 10K Canicross and a 1-mile Wild Pup. This dog-friendly, non-profit event is part of the Friends of Caledon State Park series and supports natural resources and educational programmi..

The Pocahontas Trail Festival is a trail running event held at Pocahontas State Park in Chesterfield, Virginia. It features a Half Marathon and a 10k race, both starting and finishing on a large grass field near the park's boat launch. The course was redesigned to emphasize trail running, incorporat..

Piedmont 8 Hour takes place at Powhatan State Park in Powhatan, Virginia. The event offers an 8-hour format with 2.7-mile loops, each gaining about 60 feet of elevation. The course blends open meadow running with pine forests, delivering scenic fall foliage and plenty of birdlife.Runners receive aid..

The Wilderness Run 10k is a scenic cross-country trail race held at Wilderness Run Vineyard in Spotsylvania, Virginia, situated on historic Civil War battlefields. The course features rolling hills, with the 10k consisting of two laps of the 5k out-and-back route. Participants enjoy a vibrant atmosp..

The Bivanna Trail Extravaganza is a trail running event held in Charlottesville, Virginia, featuring multiple race distances on the scenic Rivanna Trail. Participants can choose from a 40-mile full loop, a 20-mile half loop (Demibivanna), a 10-mile quarter loop (Hemidemibivanna), or a 40-mile biking..

The Heart of Virginia Council Glow Trail Run 5K is a unique nighttime trail running event held at Camp Brady Saunders in Maidens, Virginia. This family-friendly race welcomes participants of all ages and is open to everyone, not just Scouts. The course features a 5K trail illuminated with glow-in-th..

The Smithfield Hog Jog will take place in Smithfield on Saturday 25 October 2025. You can run between 5 and 5 kilometers.

Greensprings 24 is a 24-hour endurance race held in Williamsburg, Virginia, at the Greensprings venue (3751 John Tyler Hwy). The course is a USATF-certified 2.215-mile loop on crushed gravel, mostly flat and scenic, with a non-technical profile. Runners can complete full loops to reach targets such..

The Noland Trail 50K & Relay is held in Newport News, Virginia, on the scenic Noland Trail at The Mariners’ Museum Park. Location: 100 Museum Drive, Newport News, VA 23606. The event offers a solo 50K and a 2–6 person relay.The 50K route consists of six laps on the trail, with a short section added..

Harvest Hustle 10k at Walnut Creek Park in North Garden, VA, offers a cross-country trail race with a 5k option as well. The course weaves through park woods with elevation changes, rocks and roots. The 10k features three water stations at roughly miles 2.1, 3.1, and 5.2; the 5k has a water stop at..