Trail Running calendar near Williamsburg 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 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..

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..

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 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..

Haunts & Hallows is a half marathon trail race held in Virginia Beach, VA, at First Landing State Park. The course features gently rolling trails with about 300 feet of elevation gain, including roots, bridges, and sandy sections, offering scenic and varied terrain. The event fosters a supportive co..

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..

The Run for Valor 10K is a trail running event held at Valor Ranch in King George, Virginia. The race features a 10K run, a 10K weighted ruck, a 5K run, and a 1-mile fun run/walk suitable for all ages and paces. The course traverses farm trails, pastures, woods, and gravel roads, with uneven terrain..

The Pocahontas Half is a scenic running event held at Pocahontas State Park near Richmond, Virginia. It features a half marathon, 10k, and 5k race, all taking place on the forested Bright Hope Trail, which offers a soft dirt and pine needle surface with some minor hills. The half marathon course is..

Mel Williams Memorial Seashore 50K presented by Brooks is a two-loop trail race held at First Landing State Park in Virginia Beach, starting and finishing at the 64th Street boat ramp. The course runs along seashore and coastal woods, with two full aid stations at 64th Street and Bald Cypress (cuple..

The Snowy Owl 10 Mile is a trail running event held at York River State Park in Williamsburg, VA. The course features a mix of technical single-track trails, dirt fire roads, a short paved downhill finish, and scenic boardwalk sections, covering 10 miles with about 600 feet of elevation gain. Runner..

Chills In The Mill: Harwoods Half Marathon & 5K takes place in Yorktown, Virginia, starting off Oriana Road near Harwoods Mill. The event offers two distances — Harwoods Half and Harwoods 5K — with capped fields (200 for the half, 150 for the 5K). Runners encounter a mix of wide, open trail roads an..