Trail Running calendar near Keswick 2026-2027

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...

Experience rolling single track trails and diverse wildlife in Bedford Virginia. Choose between a 10k or a half marathon on intermediate wooded paths or participate remotely through virtual race options.

Experience a unique trail run through the historic former prison grounds of Laurel Hill Park. Choose between 5.4 or 10 mile distances on a course featuring meadows, forests, and old guard towers.

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 50 mile trail run along the scenic Occoquan River in Virginia during the peak of spring. This historic event features forested paths and the largest bluebell stands on the East Coast.

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 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..

Experience a scenic trail run or walk through the apple fields of Johnson's Orchard in Bedford. Support cancer wellness programs while enjoying mountain views, s'mores, and wine samples at this community fundraiser.

Run a scenic, four-lap cross-country 10k at Southern Revere Cellars. Your registration includes chip timing, a tech shirt, and a post-race beverage. The event supports a local animal rescue charity.

Choose from three scenic vineyard runs at Delfosse Winery. Tackle challenging summits for rewarding views across the 3k, 6k, or 9k courses. Virtual participation options are also available.

Run Fest at Panorama Farms offers a day of trail racing and community celebration on April 18, 2026. Choose from a 4-mile trail race, a team relay, or a 1-mile fun run, followed by a festival with live music and local food. It's a chance to..

Run through the scenic vineyards of Barrel Oak Winery on a challenging cross-country course with hills and gravel paths. Runners receive a finisher's medal, tech shirt, and a glass of wine, with proceeds supporting veterans. A virtual optio..