Trail Running calendar near Stephens City 2026-2027

Run with your dog at the Howlin' Coyote Canicross Trail Race in Caledon State Park, featuring varied terrain and a 10 km canicross plus a one mile Wild Pup dash. This non profit event supports Friends of Caledon and is disposable cup free.

Scenic trail running at Milkhouse Brewery in Mount Airy with a 5 Mile race and 4 Hour and 8 Hour ultra challenges. Presented by the Frederick Steeplechasers to honor Rick O'Donnell and raise funds for local scholarships.

Halloween Horror 5k & 10k returns to Conway Robinson State Forest Park in Gainesville, VA, offering a forest trail race with a Halloween theme. The event features 5k and 10k distances, with the 10k being two laps of the 5k course. The loop..

Fire on the Mountain is a scenic trail race in Green Ridge State Forest near Little Orleans, Maryland, on November 1, 2026. Choose a bold 50K or rugged 25K on technical trails and forest roads with aid stations and finisher perks.

Run Schaeffer Farms singletrack in Germantown on Saturday, November 7, 2026 with half marathon, 10K and 5K options. In person and virtual entries welcome; proceeds support Interfaith Works for a fun, challenging trail day.

Annapolis Striders unites runners in Annapolis, MD with road and trail races from 1 mile to ultramarathon and training programs for beginners to marathoners. Enjoy community races and a lively event calendar year round.

Enjoy a crisp fall trail run at Hemlock Overlook, winding through forests, fields, stream crossings, and scenic Bull Run views. Choose a 5 or 10 mile course with plenty of spots for friends and family to cheer.

Run the scenic Turkey Trot at The Winery at Bull Run on Manassas National Battlefield with 5k and 10k options, in person or virtual. Enjoy a post race glass of wine, a finisher medal and tech shirt while supporting the Manassas Battlefield..

Run scenic trails along the Occoquan Reservoir at Fountainhead Regional Park for the Fall Backyard Burn Trail Run. Choose a spirited 5 Mile or a challenging 10 Mile course with rolling climbs and great views.