Trail Running calendar near Chester 2025-2026

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..

2025 Wilderness Run 5k & 10k The event takes place on October 18 at Wilderness Run Vineyard in Spotsylvania, VA (11109 Plank Rd; GPS 38.325153, -77.719921). It features cross country trail courses with hills. The 5k is an out-and-back o..

Event overview The Piedmont 8 Hour is scheduled for October 18, 2025, at Powhatan State Park in Powhatan, VA. The event returns for year 10 and uses a 2.7 mile loop with about 60 feet of elevation change per loop. Event formats listed inclu..

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 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..

Event Greensprings 24 is a 24-hour endurance race on Saturday, October 25, 2025, in Williamsburg, VA (3751 John Tyler Hwy). The event benefits The Arc in Williamsburg, VA. Awards are given for completing 50k, 50 miles, 100k, 75 miles, and 1..

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 wit..

Event overview 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 inc..

Take on the scenic Noland Trail 50K in Newport News at Mariners Museum Park, solo or as a 2 to 6 person relay over six laps. All finishers get a shirt and medal and registration includes the Fall Festival with live music and craft beer.

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..

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 mara..

The Freight Train Ultra Marathon is held at High Bridge Trail State Park in Farmville, Virginia, offering distances of a half marathon, 50k, and 100k. The course is a flat rail trail with minimal elevation gain, featuring scenic views inclu..

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 tr..

Freight Train 100k/50k : Farmville, VA The Freight Train event in Farmville, Virginia offers multiple distance options on a rail trail that runs through High Bridge Trail State Park. The event uses the Train Station at 510 W. 3rd Street as..

The Tidewater Strider Dismal Swamp 50K/Marathon/Half Marathon/50K Relay takes place in Chesapeake, Virginia. The event offers five options: Dismal Swamp 50K, Marathon, Half Marathon, 50K Relay, and a Half Marathon Walkers. The USATF-certifi..

The Tinsel Trot 10k in Louisa, VA, is a festive cross-country running event held at Southern Revere Cellars. The course loops around the winery property, with the 10k consisting of four laps and the 5k two laps, featuring gentle terrain wit..

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..

Tackle the Willis River fat ass trail at Bear Creek Lake State Park on January 4, 2026, with 50K, 35K and 20K courses over rolling, sometimes wet terrain and stream crossings. Entry is free; please bring a prepackaged food donation to share..

Run the Snowy Owl 10 mile at York River State Park, a winter trail through rocky single track, boardwalks and fast fire roads with rolling climbs and aid stations. Warm drinks, a ceramic finisher medal and winter swag await at the finish.

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 t..