Trail Running calendar near Naval Academy 2026-2027

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.

The Talaria Trail Run is a fall event at Trap Pond State Park in Delaware. It features a 4.5-mile race on the scenic Bob Trail and a 2-mile walk. Participation supports Legacy Academy.

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.

Join the 28th annual Milford Cross Country Booster Reindeer Stampede 5k this November in Milford, Delaware. This long running community event features a 5 km race for all participants.

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 the rolling hills of Fair Hill Natural Resource Management Area during this winter trail event. Choose between 25K or 50K distances on beautiful single track trails with heated facilities and fully stocked aid stations.

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.

Support therapeutic riding programs while running through the beautiful forested trails of the Wicomico Demonstration Forest in this inaugural 5k trail race.

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.