Trail Running calendar near Charlottesville 2026-2027

The No Man's 50K Challenge is a women's trail running event with 25K and 50K distances on a mixed-surface course in Virginia. It features a supportive atmosphere and a generous 9-hour cutoff. The race is limited to 120 entrants.

The Winter Conway Robinson 5k & 10k takes runners through the trails of Conway Robinson State Forest Park in Gainesville, Virginia. The event, scheduled for March 7, 2026, welcomes both runners and walkers and offers on-site and virtual par..

The Naked Creek Trail Race offers 25K and 10K courses on the private, scenic trails of Panorama Farms in Virginia. Runners can experience wooded singletrack with views of the reservoir and Blue Ridge Mountains. The event provides a unique c..

The Bel Monte Endurance Runs traverse the scenic trails of Virginia's Blue Ridge Mountains in the George Washington National Forest. Runners can choose from three challenging distances on a course of single-track trails and mountain roads...

Hit the winding single track of a Bedford park for the Trail Nut Half Marathon. The course features over nine miles of rolling, wooded trails, with wildlife often spotted along the way. The park itself offers a wide range of recreational am..

Event Details The Dogwood Ultra Marathons are held every March at Twin Lakes State Park in Green Bay, Virginia. The event offers several formats: a 10 Mile race, 12 Hour, 24 Hour, and 48 Hour solo runs, and relay options for each time domai..

The Terrapin Mountain trail races in Sedalia, Virginia, offer a 50k and a Half-marathon on scenic paths. Now in its 18th year, the event includes participant swag, camping, and supports a local youth charity. It's a spring tradition for man..

A cross country 4k and 8k around Twisted Oak Farm Brewery in White Post, VA with chip timing, water stations, and a virtual option. Points count toward multiple series including Back of the Pack and Sippin' Series.

Run a scenic cross-country trail through Wilderness Run Vineyards. This event on March 21, 2026, features a 5K and a 1 Mile run, with post-race food, music, and a drink for participants over 21. Proceeds benefit St. Patrick School.

Experience a scenic cross country trail run through Wilderness Run Vineyards featuring a 5K and 1 Mile distance. Enjoy post race live music and refreshments at the winery to support St. Patrick School.

This 41-mile mountain trail race loops through the George Washington National Forest, featuring waterfalls, cliffs, and 8,000 feet of climbing. With a strict field limit and remote course, crews are not permitted. Top finishers earn cash pr..

This fundraising 5K supports the Free Clinic of Central Virginia's efforts to rebuild after a fire. The event offers in-person and virtual options on a paved trail course in Lynchburg. Participants can also fundraise for free entry and othe..

Trek across the rugged western slope of Massanutten in Virginia. Choose a distance from 7 to 28 miles, with the option to carry weight for an extra challenge. Finish within 10 hours on a course of single-track, fire roads, and ridgeline tra..

Experience a classic 50 mile trail run through Virginia's spring beauty. The course winds through rolling forested terrain along the Occoquan River and Bull Run, featuring large bluebell stands. This event, with its historic Civil War theme..

Run a scenic 5k cross-country course at a Virginia vineyard. The event welcomes runners and walkers alike and offers virtual participation options. It takes place in Warrenton on April 4, 2026.

Run a memorable 14-mile point-to-point trail adventure from one Sheetz to another. This untimed event features themed aid stations with unique snacks, supports local charities, and provides useful swag like an insulated travel mug.

Run a scenic and historic 10k on Virginia's Glenwood Horse Trail. The point-to-point course passes old mines and features a fast downhill finish. Due to limited parking, a shuttle is provided for runners.

Event Overview The Happy Camper Trail Race features a walk/run 5 km and a 10 km event. The race aims to bring the community together, promote fitness, and showcase trails in the Blue Ridge Mountains. It also supports the Campership Program,..

Run a scenic loop course along the James River in April. Choose your target distance from 10 miles to 50 miles, with a unique format that credits you as a finisher for any distance you complete. The event offers aid stations, pacers on long..

This event offers a scenic 5K run and a 3K walk through Bedford's apple orchards and countryside. Afterward, participants can enjoy wine samples and refreshments by a campfire. Awards are presented for the top finishers in the 5K race.