Trail Running calendar near Charlottesville 2026-2027

A 50 mile trail run in Clifton, Virginia on April 4, 2026, featuring forested, rolling terrain and spring bluebells. The 32nd running includes a 13 hour cutoff, a $125 entry fee, and Trail Sisters approved amenities.

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 a unique 14 mile point to point trail run through the forests of Virginia. Enjoy a flat course featuring themed aid stations serving pie and s'mores while supporting local children's charities.

A 10K trail race near Buchanan, VA on the Glenwood Horse Trail that passes old mines, limits parking to 100 vehicles, and offers a virtual option.

This backyard ultra adds a brutal twist: runners must complete a 4.167-mile loop every hour while carrying an extra pound each lap. The race goes on until only one person remains. It's a test of endurance where the load increases but the ti..

A lap-based trail event at James River State Park offering a 10 mile loop plus 50K, 50 mile solo, 50 mile relay and a night 10 mile race; loop progression determines official distances and a 16 hour cutoff applies to all.

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.

Nighttime training run of 25.9 miles on the Massanutten Mountain Trail that mirrors miles 70 to 96 of the MMT 100. Prior daytime experience on the course is required and one personal aid stop is likely near 15.2 miles.

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.

Rise Thermopylae is an immersive endurance challenge set in Virginia's wilderness. Choose from 6, 12, or 24 hour events that combine rucking, obstacles, and psychological tests. It's led by elite coaches and focuses on personal development..

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 an overnight trail relay at Pocahontas State Park featuring smooth single track and lakeside views. Form a team to run through starlit woods and enjoy a weekend of camping and community activities.

Promise Land 50K in Bedford Virginia uses the Promise Land Youth Camp as start and finish. The route includes grassy roads and downhill single track with more than 7,400 ft of elevation change and seven aid points on course.

Experience a unique run through the Metro Richmond Zoo with a choice of a 5k trail, a kids 1 mile run, or a 42 obstacle ninja challenge. All participants receive zoo admission for a day of wildlife conservation and adventure.

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.

A timed mountain-trail race at Mint Springs Valley Park in Crozet, covering about 3.9 miles with 860 ft of elevation gain. The single-track ridge course finishes by the upper lake and includes overall and age-group awards.

A spring rail trail ultramarathon in Farmville VA offering 100K, 50K and a new half marathon, low total elevation, two crossings of High Bridge, handcrafted pottery awards, and various discounts and race options.

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.