Trail Running calendar near Dayton 2025-2026

The West Virginia Trail Fest is an annual family-friendly trail running event held in May in Pocahontas County, West Virginia, known for its mountainous terrain. The festival features multiple race distances including a challenging 100K, 60K, 30K, 5K, and a 1-mile kids run. Races showcase the region..

The Dark Skies 100K is a challenging point-to-point trail race held during the West Virginia Trail Fest. Starting at Seneca State Forest, runners traverse scenic trails, including the Allegheny and Greenbrier River trails, passing notable landmarks like the Seneca fire tower and Green Bank Observato..

The Massanutten Mountain Trails (MMT) 100 Mile Run is a challenging ultramarathon held in the Massanutten Mountains within Virginia's Shenandoah Valley. Starting and finishing at Caroline Furnace Lutheran Camp in Fort Valley, VA, the rugged course features rocky trails and steep mountain climbs tota..

The Happy Tail Wine Trail 5k is a fun and inclusive running event held at 53rd Winery in Louisa, Virginia. Participants can enjoy a scenic cross-country course around vineyards, with options for a 5k race, a 1-mile fun run for children aged 5-13, and a dog jog for furry friends. The event promotes c..

The Ruff Race is a family-friendly 5K hike/run event held in the scenic Village of Snowshoe atop Cheat Mountain. Participants can run or hike with their pets through beautiful backcountry trails, enjoying varied distances with bail-out options. The race features separate start times for runners with..

The Barrel Oak 6k is a challenging cross-country running event held at Barrel Oak Winery in Delaplane, VA. Participants can choose between a 3k or 6k race, with the 6k being two laps of the 3k course. The event features scenic routes through vineyards, gravel roads, and hills.Runners receive a finis..

The Old Dominion 100 Mile Endurance Run is a challenging ultramarathon held in Fort Valley, Virginia, featuring a measured loop course through the Massanutten Mountains and Shenandoah River Valley. The race covers 100 miles with 14 significant climbs totaling 14,000 feet of elevation gain. Participa..

The Crooked Run Valley 10k is a scenic and challenging trail race held at Sky Meadows in Delaplane, VA. Participants can choose between a 5k or 10k course, with the 10k being two laps of the 5k loop. The event features chip-timed results, finisher medals, and technical event shirts.It supports the c..

The Jackson River Scenic Trail Marathon, Half Marathon, 10k, and 5k is a vibrant running event taking place in Covington, Virginia. The USATF certified course starts and ends at the Intervale Trail Head, following a scenic route along the Jackson River. Participants can enjoy a smooth, mostly flat t..

The Highlands Sky 40 Mile Trail Run is a premier ultramarathon held annually in Davis, West Virginia, primarily within the Monongahela National Forest. Starting and finishing at Canaan Valley State Park, the challenging 40-mile course traverses rugged and scenic terrain including the Roaring Plains..

The Canaan Valley Trail Run, scheduled for June 21, 2025, in Canaan Valley State Park, offers an exciting opportunity for runners of all levels. Participants can choose between a 5.9-mile single loop or an 11.8-mile double loop on the scenic Promised Land Trail. Each runner will receive a finisher m..

The 53rd Winery 5k & 10k is a scenic cross-country race held at 53rd Winery in Louisa, Virginia. Participants can choose between a 5k or 10k course, which loops around vineyards and winery grounds. The event features chip-timed races, finisher medals, technical shirts, and a complimentary glass of w..

The Leopold’s Preserve 10k is a trail running event held at Leopold’s Preserve in Broad Run, Virginia. Participants can enjoy a mostly flat dirt course with some roots, featuring scenic views of a diverse habitat and wildlife. The race is chip-timed and includes a finisher’s medal and technical even..

The Jarmans Invitational Marathon, held annually in Crozet, Virginia, is a challenging 30-mile race featuring a grueling course with 7,610 feet of elevation gain and loss. Runners tackle a steep gravel road, Jarmans Gap, five times, each lap involving a 2.9-mile climb and descent. The course is know..

The Merrie Mill Farm & Vineyard 10k and 5k is a scenic cross-country race held at Merrie Mill Farm & Vineyard in Keswick, Virginia. Participants can enjoy a course that features hills, gravel, dirt, and paved roads, with the 5k being one lap and the 10k two laps around the vineyard property. Runners..

The Third Winchester Battlefield Half, held on August 9, offers scenic trail routes through the historic battlefield. Participants can choose from a half marathon, 10k, or 5k race, with the half marathon consisting of three loops on a light gravel dirt path. The event features chip-timed results, fi..

The Orchard Dash 10k is a cross-country trail race held at Albemarle CiderWorks in North Garden, Virginia. The event features both 5k and 10k routes, with the 10k consisting of two laps on a hilly course. Participants receive a finisher’s medal, a technical event shirt, and a glass of cider from Alb..

The Inferno 10k is a challenging trail race held at Dirt Farm Brewing in Bluemont, VA. Participants navigate rugged forest trails with steep inclines, technical spots, and elevation changes, offering an exhilarating outdoor experience. The event also features a 5k race, with both distances starting..

The Odyssey Trail Running Rampage is an exciting trail running event taking place at Douthat State Park in Millboro, Virginia. Scheduled for September 6, 2025, the event features four race distances: a 50K Ultra, a Marathon, a Half Marathon, and a Six-Miler. Participants will experience challenging..

The Vineyard Vista 10k and 5k is a scenic running event held at Muse Vineyards in Woodstock, VA. Participants can enjoy a course that combines cross-country around vineyards, paved road sections, and trail segments through Seven Bends State Park. The event benefits Friends of Seven Bends State Park..