Trail Running calendar near Chesterfield 2025-2026

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..

Hosted by the Association of the United States Army Southern Virginia Chapter, the Southern Virginia 5K offers a 5K Run/Walk and a 10K Run/Walk along the Capital Trail in Charles City, Virginia. The course runs on the scenic Capital Trail with options for all paces. The event takes place at 9220 Joh..

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..

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..

Andy’s Backyard Ultra is a last-person-standing ultramarathon held at Teventrails in Earlysville, Virginia, about 14 miles northwest of Charlottesville. The event uses the Backyard Ultra format: competitors must complete a 4.17-mile lap within one hour, and laps continue hourly until only one runner..

The Smithfield Hog Jog is an annual 5K run and walk held at Windsor Castle Park in Smithfield, Virginia. The event features a 5K race with chip timing and a Kid's Piglet Run, where all young participants receive awards. The race welcomes up to 500 participants and offers awards across various age gr..

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 Indian Fields Tavern/5 Fields Brewing Co. Low Key Halloween Haunts takes place on Sunday, October 26, 2025, in Charles City, Virginia. The event offers two distances: 5k 10k The published entry fee is $20. The entry includes an official race time, a finisher's medal, and a finish-line beer. T..

The Noland Trail 50K & Relay takes place on Saturday, November 1, 2025, at The Mariners' Museum Park, 100 Museum Drive, Newport News, VA 23606. The event includes a 50K solo race and relay options, including a "Help Me Find a Team" relay. The solo event is open to ages 18 to 99. The..

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..

The Lake Anna Turkey Trot Half is a scenic and challenging running event held at Lake Anna State Park in Spotsylvania, Virginia. It features three race distances: a 5k trail run, a 10k that is half trail and half paved road, and a half marathon with a similar mixed course. Walkers are welcome, and t..

Freight Train 100k/50k is held in Farmville, Virginia, along the High Bridge Trail. The event offers 100K and 50K distances, plus a 1/2 marathon and a Half Marathon Hiker option. The course is a relatively flat rail-trail with a small initial incline; the 100K features less than 1,500 feet of total..