Trail Running calendar near Annandale 2026-2027

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.

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.

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.

An 8K cross country run at Linganore Winery in Mount Airy, Maryland on November 8, 2026. The mixed terrain course loops through grapevines and hop yards and finishers receive a complimentary tasting.

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..

The Tuckahoe 25K returns for its 8th year on November 21, 2026. This 25-kilometer trail run features a mix of single track and horse trails with three fully stocked aid stations. The event proceeds rain or shine, offering awards and swag fo..

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..

Celebrate Thanksgiving with a cross country style race through scenic Catonsville. Support the local high school running program with a chip timed 5K or a 1 Mile Family Fun Run for all ages.

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..

Experience a trail run through Fountainhead Regional Park along the Occoquan Reservoir. Choose between two distinct distances on a course featuring hiking trails and dirt roads while supporting a local non profit.

Experience a scenic out and back half marathon on the flat and smooth Dahlgren Railroad Heritage Trail. Enjoy a unique post race campfire with roasted donuts and earn a custom finisher medal.

Experience a 50 km trail run through the rolling fields and woods of Maryland featuring 5,800 feet of elevation gain. Enjoy well stocked aid stations and a heated indoor post race celebration with handmade finisher awards.