Trail Running calendar near Silver Spring 2026-2027

Experience a unique trail run through 1600 acres of former prison grounds at Laurel Hill Park. Choose between 5.4 or 10 mile distances on scenic singletrack featuring historic guard towers and open meadows.

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 scenic singletrack trails of Lake Fairfax Park with 5 mile and 10 mile race options. Enjoy a community atmosphere with post race breakfast and a dedicated program for children.

The Patapsco Valley 50K offers a scenic trail run near Baltimore. Finishers earn unique awards, like a hand-thrown mug for the 50K. A virtual option lets you run your own course during the month following the event.

Experience a seasonal trail run or walk through the scenic Conway Robinson State Forest in Gainesville with 5k and 10k distance options for all participants.

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

Experience a mix of twisty singletrack and open farm field running in Germantown. This late autumn trail event offers three distances and a festive post race atmosphere at the historic Button Farm.

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 at Riverbend Park with 5 and 10 mile trail races. This event offers scenic Potomac River views, a dedicated kids program, and professional race support in a beautiful natural setting.

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 Reindeer Stampede 5k at Killens Pond State Park for a run or competitive walk. This established event supports local cross country and features festive awards and a post race party with seasonal treats.

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 the beauty of Fountainhead Regional Park on a course featuring hiking trails and dirt roads. With two distance options and a dedicated program for kids, this event offers a complete day of trail running near the Occoquan Reservoi..

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.