Trail Running calendar near Keezletown 2026-2027

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.

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..

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.

A loop-based trail event at James River State Park offering 10 mile loops, 50K and 50 mile distances, relays, a night 10 miler, hiker categories, and roughly 1025 feet of climbing per loop.

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..

A spring festival at The Yew Mountain Center with a 5K fundraiser run and a one mile fun run. The day also offers wildflower walks, a basket workshop, native plants, local food, live music and vendors.

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.

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.

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 100 mile trail ultramarathon in the Massanutten Mountains of Virginia with over 18,000 feet of ascent, a 36 hour cutoff, and organizational support including a Participants’ Guide, training runs, and volunteer staffing.

A family-oriented trail running weekend in Snowshoe, WV featuring races from a kids mile to a 100K through state parks and national forest, plus movie night, markets, live music, and fireworks.

West Virginia Trail Fest is a family friendly trail running festival each May around Snowshoe in Pocahontas County, with scenic forest and single track races for all ages. Enjoy kids activities, a historic train ride and community fun.

Run or walk a scenic off road 5K course along the Cacapon River and Lewis Farm. This benefit event supports local youth programs while celebrating the Wardensville Spring Fest with local food and creativity.