Trail Running calendar near Woodstock 2025-2026

The Orchard Dash is a cross‑country trail race at Albemarle CiderWorks in North Garden, Virginia. Runners choose between 5k (two laps) and 10k (four laps) on a hilly, wooded course that differs from the winter route. The event blends competition with a festive atmosphere: finishers receive a glass o..

The High Rock Mountain Running Challenge is a Cascade, Maryland race starting and finishing at Pen Mar Park (14600 Pen Mar Rd). The course covers about 3.8 miles, including roughly 1.8 miles of ascent to High Rock Overlook before a descent back to the park for the finish. The route offers a pictures..

The Inferno 5k & 10k at Dirt Farm Brewing in Bluemont, Virginia, challenges runners with a forest-trail course behind the brewery. The 5k is a single loop; the 10k doubles back on the same path, featuring tree roots, rocks, and elevation changes that test footing and lungs. Expect steep climbs, rapi..

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 Tails on Trails 5K Run/Walk takes place at Cacapon State Park in Berkeley Springs, West Virginia. This early fall event features an easy 5K course along the Rock & Roll Trail, suitable for runners and walkers of all levels. The scenic trail highlights the natural beauty of the area, making it a..

Vineyard Vista 5k & 10k takes place at Muse Vineyards in Woodstock, Virginia. The course blends vineyard cross‑country with a paved road segment and trail loop around Seven Bends State Park; the 5k is a single loop and the 10k uses two loops. The event offers a winery atmosphere, with participants e..

Athletic Equation will host its 18th Annual 12-Hour Adventure Trail Run at Prince William Forest Park, a 17,000+ acre, 40-mile trail reserve near Triangle, VA. The event covers 30 kilometers on a 6.5-mile looped figure-eight trail course, run for up to 12 hours with a two-person relay. The 100% trai..

Valley View Hard Cider Challenge Half, hosted by Bishops Events, takes place at Valley View Farm in Delaplane, Virginia. The event offers 5k, 10k, and Half-Marathon distances on knotty courses that blend cross-country, trail, and hills. The 5k and 10k are out-and-back once, while the Half is out-and..

Grindstone Running Festival by UTMB is an East Coast trail event staged at Natural Chimneys Park in Virginia, just west of the Shenandoah Valley. Runners choose from four distances: 100M, 100K, 50K, and 21K, with a highly technical course that climbs ridges and peaks through the George Washington an..

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 a challenging trail running event held at Seven Bends State Park in Woodstock, Virginia. It features a roughly 10-mile loop course with mixed terrain including gravel roads, two-track dirt roads, and single-track trails, with about 1800 feet of elevation gain per loop. The r..

Laural Ridge Community College 5K is a multi-surface cross-country style race/walk held on the Middletown Campus in Middletown, Virginia. The start and finish are outside the Student Union Building on Garland Snapp Drive. The 5K course includes a shorter lap around the back fields, a second lap arou..

9K for Semper K9 is a community running and walking event in Fredericksburg, Virginia, held at Old Mill Park along Canal Path by the Rappahannock River. The program includes a 9K race and a Kids .9 Mile Fun Run, welcoming runners, walkers, families. The course runs along canal paths in downtown Fred..

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 gains but no major climbs. Runners can choose between 5k and 10k distances, with the 10k route bein..

The Lake & Leaf Shuffle is a trail running event held at Deep Creek Lake State Park in Swanton, Maryland, typically scheduled in late September to coincide with peak fall foliage. Participants can choose between a 6-mile single loop or a 12-mile double loop on scenic trails, offering a challenging a..

River's Edge Endurance Challenge is a nonprofit running event held at Brunswick Middle School, Maryland. The lineup includes a 5K (3.1 miles), a 3-Hour Endurance Race, and a 6-Hour Endurance Challenge. The largely trail-based course runs on the River's Edge Trail System, with about a mile on school..

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 varied terrain for runners. Participants also have the option to run a 1-mile distan..

Quantico 24-Hour Walk, Run & Relay for Charity is held in Quantico, Virginia, benefiting Semper Fi & America's Fund, which supports wounded service members and military families. The event invites walkers, runners, and relay teams to cover mileage by doing laps or jogging several miles, with team an..

The Fall Harvest 5k is a scenic trail race held at Claude Moore Park in Sterling, Virginia. Set amidst the vibrant colors of autumn, the course features forest paths and leaf-covered trails, offering a picturesque experience for both runners and walkers. This event is part of the Run Your PRCS Parks..

West Virginia Trilogy is a three-day stage trail race set on and around Spruce Knob, West Virginia’s highest peak, in the Monongahela National Forest near Circleville. The event comprises Day 1: 50k, Day 2: 50 miles, and Day 3: 13.1 miles, with a full trilogy option that combines all three. Race HQ..