Trail Running calendar near Winchester 2025-2026

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..

Trails 4 Tails in Hanover, PA, is a trail running event held at scenic Codorus State Park, featuring a 5.72-mile loop course around Lake Marburg with single track trails and shoreline views. The event offers three race options: a 40 Mile Ultra (7 loops, ~4,200' elevation gain), a 40 Mile Relay (team..

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..

The Rock 'N The Knob Trail Challenge, held in Claysburg, Pennsylvania, is the state's highest trail race, taking place atop Blue Knob Mountain at over 3,100 feet elevation. The event offers three challenging courses: a 10K "Short Course" with steep climbs and technical terrain, a 20K-25K "Medium Dis..

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..

The Creation House 5K Rugged Trail Run is a 5K trail race held in Littlestown, Pennsylvania (165 Christ Church Rd). It supports Creation House, a program designed to keep homeless families together as they rebuild their lives. The course is described as a beautiful, rugged nature run through farmlan..

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..

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..

Chase the Cougar 5K is a Run/Walk held in Somerset, Pennsylvania, on the grounds of the Somerset Historical Center at 10649 Somerset Pike. The cross country course was engineered by Dave Mapes. Proceeds benefit the North Star Cross Country team.Preregistration includes a race T‑shirt, and shirts wil..

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..

St. Anselm's Family 5k is a family-friendly fundraising race in Washington, DC, held at 4501 South Dakota Ave NE. The event covers a 5k distance on a double-loop trail course, suitable for runners and walkers alike.It benefits a memorial scholarship fund at St. Anselm's Abbey School, supporting stud..

Mountain Creek Mayhem takes place at Pine Grove Furnace State Park in Gardners, PA, within Michaux State Forest in the northern Appalachians. The event offers 50K, 20-Miler, and Half Marathon distances, featuring flowy single-track, ridgelines, rocky descents, and sweeping views. Elevation gains run..

The Laurel Highlands Ultra - Fall Classic is a challenging 50K trail race held in Somerset, Pennsylvania, along the scenic Laurel Highlands Hiking Trail. The 2025 event features a point-to-point course starting at Laurel Summit State Park and finishing at Rt 56 in Seward, showcasing rugged terrain w..

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..