Trail Running calendar near Dayton 2026-2027

The Terrapin Mountain will take place in Big Island on Saturday 21 March 2026. You can run between 13 and 31 miles.

Experience a scenic run through the landscape of Twisted Oak Farm Brewery in White Post. This event features 4k and 8k distances followed by a post race beverage at the brewery.

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..

Choose your challenge at UltraTrax Massanutten with distances ranging from 7 to 28 miles. Hike or ruck through the scenic Shenandoah Valley on a rugged course featuring forested singletrack and panoramic ridgeline views.

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.

Experience the backcountry of Buchanan Virginia on the Glenwood Horse Trail. This event features a point to point course past historic mines and through technical rock gardens with a shuttle to the start line.

Experience a hilly and technical trail race through the scenic property in Bluemont Virginia. Choose between the 5k and 10k distances and enjoy a glass of beer after conquering the technical terrain.

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..

Join the Sip & Stride 5k and 10k in Louisa Virginia for a chance to earn points in the Sippin’ Series. Choose between in person racing or multiple virtual participation options with medals and shirts.

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..

Experience the scenic grounds of Barrel Oak Winery in Delaplane, Virginia, through 3k and 6k race options. This inclusive event welcomes both walkers and leashed pets for a day of activity in a beautiful vineyard setting.

Experience the scenic trails of Third Winchester Battlefield Park with 5k, 10k, and half marathon distances. This historic Virginia event welcomes both runners and walkers for a beautiful spring race.

Run a scenic 5k around the Bluemont Station Brewery property in Virginia. The event welcomes both runners and walkers and offers in-person and virtual participation options.

The Perfect Day 50K takes place on the Massanutten Western Slope in Keezletown, Virginia. Runners can compete individually or as part of a two or three person team on a Saturday in May. The event offers a full day on the trails.

Experience four distinct trail races across Charlottesville and Crozet in this summer series. Compete for age group awards and finisher shirts while running through scenic venues like Mint Springs and Pen Park.

A demanding 100-mile trail ultra through the rocky Massanutten Mountains, featuring over 18,000 feet of climbing. Known for its friendly aid stations and well-marked course, it takes place in Virginia's Shenandoah Valley.

West Virginia Trail Fest is an annual May celebration of trail running in the mountains of Pocahontas County. Races from a 5K to a 100K explore state parks, historic sites, and fire towers. The weekend also features family activities, local..