Trail Running calendar near Woodstock 2025-2026

Grindstone Running Festival by UTMB is a trail ultramarathon event held at Natural Chimneys Park near the Shenandoah Valley in Virginia. The festival offers four distances—100M, 100K, 50K, and 21K—tracing routes through the George Washington and Jefferson National Forest with steep climbs, ridges, v..

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..

The West Virginia Trilogy is a three-day stage race on and around Spruce Knob, on the Eastern Continental Divide. It takes place over Columbus Day weekend, October 10–12, 2025, and is hosted by the West Virginia Mountain Trail Runners with race headquarters at the Spruce Knob Mountain Center’s 400-..

The Full Distance 10k is a scenic trail running event held at Locust Shade Park in Triangle, Virginia. The course features a mix of trails and pavement, with about 40% paved and some hills, consisting of four loops for the 10k distance. This chip-timed race welcomes both runners and walkers and is p..

The Trails 4 Miles is an annual trail running event held at Sherando Park in Stephens City, Virginia. The main race is a challenging 4-mile course featuring mixed surfaces, including paved paths and wooded trails through the scenic Sherando Park Mountain Bike Trails. Runners experience beautiful fal..

MoCo Dems 5K Fall FunRun is a 5K run/walk at Agricultural History Farm Park in Derwood, MD. Organized by the Montgomery County District 15 Democratic Caucus, it offers a 5K for adults, a Youth 5K, and a free option for youth 10 and under. The course is a natural trail through the park, with water st..

Rocky Gap 25K, 50K, Relay Trail Run takes place at Rocky Gap State Park in Flintstone, Maryland. The race features three scenic loops—Loop A (Rocky Trail, 6.5 miles), Loop B (Canyon Overlook, 4.4 miles), Loop C (Lakeside Loop, 5.2 miles). The 25K covers A–B–C once (about 16 miles); the 50K covers al..

Boulder Dash at Pinesburg Quarry is a running event hosted by Martin Marietta in Williamsport, Maryland. It offers a 5 Mile Challenge, a Family Friendly 5K, and a 1 Mile Fun Run for all levels. The 1 Mile Fun Run and 5K travel on rolling roads and packed gravel around the quarry; the 5 Mile goes int..

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, with the 10k consisting of two laps of the 5k out-and-back route. Participants enjoy a vibrant atmosp..

The Bivanna Trail Extravaganza is a trail running event held in Charlottesville, Virginia, featuring multiple race distances on the scenic Rivanna Trail. Participants can choose from a 40-mile full loop, a 20-mile half loop (Demibivanna), a 10-mile quarter loop (Hemidemibivanna), or a 40-mile biking..

The Westover 5k & 10k takes place on October 18, 2025, at Bon Air Gardens in Arlington, VA. Distances offered: 5k 10k The event awards points toward the Year-Long 5k, 10k, and Back of the Pack Series, and toward the Fall Series. A virtual run option is available. Walkers and strollers are wel..