Trail Running calendar near Stuarts Draft 2025-2026

The Twisted Trail 10k is an annual trail running event held in Forest, Virginia, at the New London Tech Trails. The 2025 race, its fifth edition, features a 10-kilometer course running through three loops—Orange, Blue, and Green—on well-maintained trails with minimal trip hazards. Due to constructio..

The 53rd Winery 5k & 10k is a scenic running event held at 53rd Winery in Louisa, Virginia. The course is a cross-country route looping around the vineyards and winery property, featuring a fairly flat terrain with some elevation changes. The 5k consists of three laps, while the 10k covers six laps...

The Jarmans Invitational Marathon is a challenging 29-mile race held in Crozet, Virginia, typically on the first or second Saturday of August. The course consists of five laps up and down Jarmans Gap Road, a steep gravel road with 7,610 feet of total elevation gain and loss. Runners face tough condi..

The Merrie Mill Farm & Vineyard 10k is a scenic cross-country race held at Merrie Mill Farm & Vineyard in Keswick, Virginia. The course features a mix of flat gravel, dirt, and paved roads with some notable hills, offering one lap for the 5k and two laps for the 10k. Walkers are welcome, and a virtu..

The Camp Bethel PEP! 5K Run is an annual trail running and walking event held at Camp Bethel, located at 328 Bethel Road, Fincastle, Virginia. The 9th edition is scheduled for August 30, 2025. The 5K course traverses diverse terrain including trails, fields, and forests across the camp's 470-acre pr..

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 Odyssey Trail Running Rampage is a trail running event held at Douthat State Park in Millboro, Virginia. Scheduled for September 6, 2025, it features four race distances: 50K, Marathon (26.2 miles), Half Marathon (13.1 miles), and a Six-Miler (6 miles). The courses are looped, showcasing challen..

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..

The Helvetia 10k Mountain Run is an annual race held in Helvetia, West Virginia, a small Swiss mountain community in southern Randolph County. Celebrating its 26th running in 2025, the event features a 6.2-mile course on country roads and trails that follow portions of an original Swiss settlement t..

The Grindstone Running Festival by UTMB is a premier trail running event held in Natural Chimneys Park, Virginia, just west of the Shenandoah Valley. Set amid the George Washington and Jefferson National Forests, the festival offers four challenging race distances: 100 miles, 100 kilometers, 50 kilo..

The Pawpaw 10 Miler and 5 Miler take place at Powhatan State Park in Powhatan, Virginia, featuring scenic runs along the James River, through open fields, shaded forests, and past historic cabin ruins. The event offers a 10-mile race and a shorter 5-mile option, both incorporating diverse terrain in..

The Woodstock Warrior is an endurance trail running event held at Seven Bends State Park in Woodstock, Virginia. It features a challenging 10-mile loop course with mixed terrain, including gravel roads, two-track dirt roads, and single-track trails, with approximately 1,800 feet of elevation gain pe..

The Brandy Station Battlefield 10k is a trail running event held at Brandy Station Battlefield in Virginia. The course combines cross country terrain with gravel dirt roads, featuring slight elevation changes but no major climbs. Runners can choose between 5k and 10k distances, with the 10k route be..

The Fox Trot 5k in Keswick is a scenic cross-country race held at Merrie Mill Farm & Vineyard. The event features a 5k course that includes a mix of flat gravel, dirt, paved roads, and some notable hills, offering a challenging yet picturesque run around the winery property. Participants can also ch..

The Greenbrier River Trail Marathon is an annual running event held in West Virginia, featuring a full marathon (26.2 miles) and a half-marathon (13.1 miles). The marathon course is a scenic, point-to-point route that starts at Cass Scenic Railroad State Park and finishes at Stillwell Park in Marlin..

The West Virginia Trilogy is a challenging three-day stage race held in Circleville, WV, on Spruce Knob, the state's highest peak, within the Monongahela National Forest. The event features three distances: a 50-kilometer run on day one, a 50-mile run on day two, and a 13.1-mile half marathon on day..

The Piedmont 8 Hour is an annual trail running event held at Powhatan State Park in Powhatan, Virginia. Celebrating its 10th year, the race features a 2.7-mile loop with about 60 feet of elevation change, winding through open meadows and pine forests with scenic fall foliage. The course is mostly ru..

The Wilderness Run 10k is a scenic cross-country trail race held at Wilderness Run Vineyard in Spotsylvania, Virginia, situated on historic Civil War battlefields. The course features rolling hills and consists of two laps of a 5k out-and-back route. Participants enjoy a vibrant atmosphere with post..

The Into the Darkness Night Trail Run is a unique 4-mile night race held in Roanoke Valley's Explore Park. The course features a mix of twisty, rolling single-track trails and grassy, gravel roads, primarily on IMBA-designed trails. Runners navigate the route marked with reflective arrows and glow s..

The Chessie Trail Marathon, held annually in Lexington, Virginia, offers a scenic and flat course along the Chessie Nature Trail, a top-rated rail trail in the Shenandoah Valley. Participants can choose from a full marathon, half marathon, 10K, 5K, or a 26.2-mile relay. The trail runs beside the Mau..