Trail Running calendar near Chester 2025-2026

Celebrate the 30th Chesterfield Alumni Run on Thanksgiving at Pocahontas State Park with a free community XC 5k and kids fun run with gingerbread cookies. Stay for giveaways and optional donations to support local track and cross country.

Celebrate Thanksgiving at the Lake Anna Turkey Trot on November 28, 2025 at Lake Anna State Park. Run a 5k, 10k or half marathon on scenic trail and road courses with a tech shirt, finisher medal and chip timing, or join virtually.

Run the After Ate 8K and 2 Mile in Williamsburg on Nov 29, featuring chip timed races, competitive walk and ruck options, and a custom long sleeve shirt. Finishers get pizza, a local beer and a chance to support a community food drive.

Run the scenic High Bridge Trail in Farmville on December 6 with options from half marathon to a challenging 100k. Flat rail trail, aid stations, finisher awards and a friendly small race vibe for newcomers and ultrarunners.

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..

Run the Freight Train on Saturday December 6 2025 in Farmville Virginia, with distances from half marathon to 100K on a scenic rail trail. Cross the iconic High Bridge twice and earn a handcrafted pottery finisher award.

Join the Tidewater Strider Dismal Swamp in Chesapeake VA on Dec 7, 2025 for 50K, marathon, half marathon, relays and a walkers option on scenic out and back looped trails. Aid stations, finisher apparel and post race pizza and beer await.

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..

Run the Pocahontas 5k, 10k or half marathon on Dec 13 along the scenic Bright Hope Trail in Pocahontas State Park. Walkers and virtual runners welcome with chip timing. Finishers get a coin and shirt and proceeds benefit Operation Turbo.

Join Dash through the Hills on Dec 13, 2025 at Hardware Hills Vineyard for a scenic charity trail 5K or 1.1 mile walk benefiting Caring for Creatures animal sanctuary. Finish at the tasting room with live music, a food truck and wine for pa..

Tackle the Snowy Owl 10 mile trail at York River State Park for a mix of technical single track, fire roads and a scenic boardwalk finish. Expect rocky twists, 600 feet of climbing and a pottery medal plus a winter hat for registered runner..

Join Willis River on Jan 4, 2026 at Bear Creek Lake State Park for free 20K, 35K and 50K trail runs. Expect stream crossings, rolling hills and wet, rugged trail on a friendly, casual fat ass style event with shared packaged snacks.

Hit the trails on January 10, 2026 in Palmyra VA for the Burke Creek Barn Burner, offering 5K and 15K trail distances. Enjoy on site coffee, finish line food and awards for a fun community race organized by the CATs.

Run laps on a certified 3.75 mile loop through scenic Sandy Bottom Nature Park in Hampton, Virginia. Pick 8 hour or 4 hour timed options in a cupless format and earn a homemade medal for a friendly, rugged training day.

Enjoy The Chills in the Mill at Harwoods Mill Park in Yorktown with a scenic half marathon or upbeat 5K over mixed trail roads and single track. Small fields, on site awards and aid stations make this a welcoming winter race.

Run the Dahlgren Trail Half Marathon in King George VA on January 31, 2026. Flat, smooth former railroad bed, aid stations and a custom finisher medal while supporting local trail volunteers.

Challenge the figure 8 trails at Lake Anna State Park in the 18th annual ICY 8, featuring an 8 hour adventure trail run and a Half Marathon+ on a looped course. Runners and hikers are welcome with scenic single and double track and generous..

Hit the scenic hilly 5k or 10k across historic Chancellorsville and Wilderness battlefields on February 14, 2026. Walkers welcome, proceeds benefit Semper Fi and America's Fund, and finishers enjoy a beer or wine plus a commemorative medal.

Run scenic trails around Holiday Lake in Appomattox with 10K, 25K and 50K options. Enjoy single track, rolling climbs, frequent aid stations, cozy camp lodging, finishers gear and a communal post race lunch.

Join RRRC in February 2026 at Bear Creek Lake State Park for Bear Creek 10 Mile and 4.2 Mile Mini Trail Runs, offering in person races plus a virtual 10 Mile option. Tackle scenic single track and multi use trails while supporting the park.