Trail Running calendar near Dayton 2025-2026

April 18, 2026, Sip & Stride 5k & 10k returns to Southern Revere Cellars in Louisa, Virginia, for a winery-style cross-country race. The 5k is two laps and the 10k four laps around the winery property, featuring mostly flat terrain with no..

Mountain & Vine Vineyard 3k, 6k, & 9k takes place at Mountain & Vine Vineyards in Faber, Virginia (500 Delfosse Winery Ln.). The course loops the winery property: 3k is one lap, 6k two laps, and 9k three laps, delivering a hilly but scenic..

Run through vineyards at Barrel Oak Winery on 3k and 6k cross country courses with gravel and rolling hills. Enjoy a finisher medal, tech shirt and a glass of wine while supporting Semper Fi and America's Fund, virtual option available.

Lace up for the Bluemont Station Brewery and Winery 5k on April 26, 2026, a three lap cross country run around scenic winery grounds with some rolling hills. Walkers are welcome and a virtual option lets you join from anywhere.

Challenge yourself on the Massanutten Mountain Trails 100 Mile Run, a rugged trail ultramarathon in Virginia with more than 18,000 feet of climbing. Expect rocky singletrack, well stocked aid stations, and a 36 hour cutoff.

Join the family friendly West Virginia Trail Fest in Snowshoe Village for scenic mountain races from a kids mile to 100K. Enjoy stunning summits, local vendors, a historic railroad ride and a fun post race party.

The Dark Skies 100K is a challenging point-to-point trail race held in Pocahontas County, West Virginia, as part of the West Virginia Trail Fest. Starting at Seneca State Forest headquarters, the course features stunning views as runners pa..

The Old Dominion 100 Endurance Run, held in Fort Valley, Virginia, is a challenging 100-mile race featuring a diverse course that includes pavement, gravel roads, single-track trails, ATV trails, logging roads, rocks, streams, and mud. This..

Choose from marathon, half marathon, 10k, or 5k on the USATF certified Jackson River Scenic Trail in Covington Virginia, a mostly flat crushed gravel route with river views. Finishers receive commemorative medals and awards.

Experience Highlands Sky 40M, a rugged 40 mile ultramarathon through West Virginia's Monongahela National Forest and dramatic Dolly Sods. Based at Canaan Valley in mid June, expect wild mountain trails and unforgettable views.

Hit the forest trails at Dirt Farm Brewing on August 29, 2026 for the Inferno 5k and 10k. Tackle a scenic, technical loop, earn a finisher medal and a Dri FIT shirt, and toast with a glass of Dirt Farm beer. Virtual option available.

Take on the Odyssey Trail Running Rampage at Douthat State Park on September 12, 2026, with four loop distances from six miles to 50K on rugged trails with steep climbs. Expect chip timing, a performance shirt, finisher pint mug and post ra..

Halloween Horror 5k & 10k returns to Conway Robinson State Forest Park in Gainesville, VA, offering a forest trail race with a Halloween theme. The event features 5k and 10k distances, with the 10k being two laps of the 5k course. The loop..