Trail Running calendar near Woodstock 2025-2026

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 Leopold's Preserve 10k is a trail running event held at Leopold’s Preserve, a 380-acre nature conservancy in Haymarket, Virginia. The course features mostly flat, dirt paths with some roots, offering a scenic and natural running experience. The 10k route is an out-and-back course with a detour o..

The 868 Estate Vineyards 10k and 5k is a scenic cross-country race held at 868 Estate Vineyards. Participants can choose between a 5k or 10k course around the vineyard property, featuring hills and beautiful views. The event includes a finisher medal, technical event shirt, and a glass of wine.Point..

The Blue Crab Bolt Trail Run at Schaeffer Farms in Germantown, MD, is a trail running event featuring 5K and 10K distances. Held at the scenic Button Farm Living History Center, the course offers a mix of flowy, fast, and fun trails with twisty single-track paths, stream crossings, log ramps, some h..

The Blue Crab Bolt Trail Run at Little Bennett Regional Park in Clarksburg, MD, offers a scenic and challenging trail running experience on August 2, 2025. Set in a 3,600-acre park with over 20 miles of trails, the event features 5K (3.7 miles) and 10K (6.2 miles) races along twisty single-track hik..

The Jarmans Invitational Marathon, held annually in Crozet, Virginia, is a challenging 29-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 with 1,522 feet of ascent. The..

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 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 Miner's Lady 8-Hour is an endurance running event held in Harpers Ferry, West Virginia, where the Blue Ridge Mountains meet the Shenandoah River. Participants run a challenging 10K loop featuring 850 feet of elevation gain, primarily on single-track trails that pass waterfalls and creek crossing..

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 running event held at Dirt Farm Brewing in Bluemont, Virginia. The course features rugged forest terrain with steep inclines, descents, and technical sections including tree roots and rocks. The 10k race consists of two loops of a winding trail behind the brewe..

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 VHTRC Women's Half Marathon will take place in Fairfax Station on Saturday 13 September 2025. You can run between 7 and 13 miles.

The 12 Hour Adventure Trail Run takes place at Prince William Forest Park near Triangle, Virginia. This challenging event features a 6.5-mile figure-eight loop course on 100% trail terrain, including single track and fire roads, with approximately 650 feet of elevation gain per loop. The course offe..

The Valley View Hard Cider Challenge Half is a scenic and challenging race held at Valley View Farm in Delaplane, VA. Participants can choose from a half marathon, 10k, or 5k course, featuring cross-country, trail, and hill segments. The event offers a festive atmosphere with a finish line cider, fi..

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 Final Countdown Tribute is an exciting running event hosted by 2 Lowe Run Company at Amani Brewing in Martinsburg, WV. This unique race features a 1.33-mile loop course where participants must complete laps within a progressively decreasing time limit. Starting with a 20-minute lap, the time sho..

The Woodstock Warrior is a challenging trail running event held at Seven Bends State Park in Woodstock, Virginia. The race features a roughly 10-mile looped course with mixed terrain, including gravel roads, two-track dirt roads, and single-track trails, with about 1,800 feet of elevation gain per l..

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..