Trail Running calendar near Keswick 2026-2027

Run on the flat, scenic dirt trails of Leopold's Preserve in this 5k and 10k event. Participants receive a medal, shirt, and chip timing, with points counting towards several annual series. A virtual race option is also available.

A cross-country 5k and 10k at Albemarle CiderWorks featuring chip timing, a finisher medal, technical shirt and a glass of cider; proceeds support Rikki's Refuge.

Experience the mountain trails of Douthat State Park with four race distances ranging from six miles to a 50K ultra. Runners will navigate waterfalls and climbing sections within the scenic Virginia State Park Adventure Series.

Run through a scenic 1000 acre farm bordering the Rappahannock River followed by live music and craft beer at Creekside Farm Brewery. Enjoy chip timed 5K or 8K trail courses with custom swag and local food trucks.

Conquer a challenging 10-mile loop at Seven Bends State Park in this multi-distance trail event. Choose from a 100-miler, 50-miler, 50k, 10-miler, or a Last Man Standing Ruck format. It's a cup-less race where strategy and resilience meet s..

Run or hike the scenic trails of Powhatan State Park along the James River. This event celebrates the native pawpaw fruit with a festival featuring live music. It's a benefit for the Friends of Powhatan State Park.

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.

Experience a dog friendly trail race through the varied terrain of Caledon State Park. Run a 10K or 1 mile course with your leashed companion to support local natural resources and educational programming.

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.

Experience the scenic beauty of Pocahontas State Park at this trail festival featuring a loop course 10k and half marathon. Enjoy runnable trails and professional timing in a picturesque Virginia forest setting.

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..

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.

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..

Trek across the rugged Blue Ridge slopes of Virginia with four distance options ranging from 7 to 28 miles. This timed mountain event features scenic single track trails and a post trek celebration at the base camp.

Experience a flat and fast USATF certified marathon on the scenic Chessie Nature Trail. This Boston Qualifier features river views and limestone cliffs with no road crossings or pavement.

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..

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..

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..