Trail Running calendar near Woodstock 2026-2027

Join the 7th annual Trails 4 Miles for a fall challenge at Sherando Park. Choose from a mixed-surface 4-mile trail run, a new mountain bike time trial, or a one-mile fun run/walk. All proceeds support the I'm Just Me Movement.

Join a community 5K run and walk through the scenic trails of Agricultural History Farm Park. Enjoy a morning of music and fitness with events for all ages and awards for top finishers.

Experience a technical trail race with your dog at a scenic equine rehabilitation facility in Virginia. Enjoy distances from 1.25 miles to 10K followed by a finishers festival with food trucks and a biergarten.

The West Virginia Trilogy is a three-day running challenge in the Monongahela National Forest. Runners complete a 50k, 50-mile, and half-marathon over consecutive days on the Eastern Continental Divide. The event is based at the Spruce Knob..

Experience a unique trail event at Milkhouse Brewery in Mount Airy featuring a 5 mile race and timed ultra challenges. Complete as many loops as possible over four or eight hours on this scenic farm course.

Experience the beauty of Western Maryland at Rocky Gap State Park with 25K and 50K trail races. Run solo or join a relay team to navigate three distinct loops featuring scenic lake views and ridge traverses.

Experience a scenic trail run at Lake Fairfax Park in Reston featuring singletrack loops with lake views. Choose between 5 or 10 mile distances while supporting local families through a community charity partnership.

Run through the forest trails of Conway Robinson State Forest for the Halloween Horror 10k. This chip-timed trail race offers series points and supports a local soup kitchen. Walkers are welcome, and a virtual option is available.

Experience a scenic 5K cross country run through the historic Rocklands Farm Winery followed by an after party with live music and wine.

The Shenandoah Zombie Run is a unique 5K survival challenge at Camp Shenandoah. Runners dodge zombies on a trail course through the woods and hills, trying to keep the flags on their belt. Everyone gets a medal, declaring them either a Surv..

Trail runners head to Maryland's Green Ridge State Forest for the Fire on the Mountain 50K and 25K races. The event features technical trails, forest roads, and strict cutoff times. It's scheduled for November 1, 2026, with a training run o..

Experience the singletrack trails of Schaeffer Farms in Germantown Maryland. This event features half marathon 10K and 5K trail races staged at a private farm with opportunities to support local charity work.

About the Event The Mountain Masochist Trail Run (MMTR) takes place in Montebello, Virginia. The race begins and ends at the Montebello Campground on Crabtree Falls Highway. Course Details The course is run in a reverse direction from histo..

Experience a 50 mile trail race through the scenic Seneca Greenway and Muddy Branch trails in Maryland. This event features forested single track terrain and small stream crossings for dedicated distance runners.

Take on a trail run through Walnut Creek Park with both 5k and 10k options. Your participation supports Rikki's Refuge, and you'll earn points in the organizer's annual race series. Runners receive a tech shirt, finisher's medal, and chip t..

Experience a scenic trail race through the forests and fields of Hemlock Overlook Regional Park. Choose between 5 or 10 mile distances on a spectator friendly course featuring stream crossings and riverside trails.

Run through the vineyards at Barrel Oak Winery on this pre Thanksgiving cross country course. The event features a 3k and 6k race, with participants receiving a finisher's medal, tech shirt, and a post race drink. The race supports Warriors..

Experience riverside singletrack and scenic views at Riverbend Park. Choose between 5 and 10 mile trail races on a course featuring rolling hills and stunning Potomac River landscapes.

Run a scenic Turkey Trot through the historic trails of Manassas National Battlefield. Choose between a 5k or 10k trail course and finish with a glass of wine from the Winery at Bull Run. Your participation supports the preservation of the..

Devil Dog Ultras features 100-mile, 100K, and 50K trail races on a loop course in Prince William Forest Park. With fully stocked aid stations and a unique loyalty challenge, it's an event built for the trail community. Registration for the..