Trail Running calendar near Woodstock 2025-2026

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, offers a challenging and scenic trail running experience with 5K and 10K race options. Set on well-maintained, flowy trails featuring twisty single-track paths, stream crossings, log ramps, hills, and open farm fields, the course is..

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 wooded park with over 20 miles of trails, the event features 5K (3.7 miles) and 10K (6.2 miles) races along twisty single-tr..

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 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 the scenic Shenandoah Valley, Virginia, featuring challenging courses through the George Washington and Jefferson National Forests. Set against stunning fall foliage and mountain views, the festival offers four race dis..

The Final Countdown Tribute is a unique running event held at Amani Brewing in Martinsburg, WV. The race features a 1.33-mile loop on a smooth, well-maintained grass trail with gentle hills. Runners must complete each lap within a decreasing time limit, starting at 20 minutes and shortening by 20 se..

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 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 Full Distance 10k and 5k is a scenic trail race held at Locust Shade Park in Triangle, VA. Participants can choose between a 5k or 10k course, with the event featuring chip timing, finisher medals, and technical event shirts. The course includes trail segments with some roots and hills, and wate..