Trail Running calendar near Sykesville 2026-2027

The Rick O'Donnell Memorial Ultra Challenge offers a 5-mile trail run plus timed 4-hour and 8-hour events. Held at Milkhouse Brewery in Mount Airy, MD, it supports a local running club's scholarship fund.

Delaware Trail Fest celebrates the state's trails at Lums Pond State Park with a unique, fully age-graded race format. Choose from a 12-hour solo run, a 12-hour relay, a 24KM, or a 12KM lap course around the lake. All finishers get a sweats..

Choose your challenge on the scenic trails of Lake Fairfax Park. Run a 5.1-mile lap or double it for a 10-mile test on singletrack paths with natural features. Support a local charity while tackling this trail run.

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.

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.

Trail runners head to Maryland's Green Ridge State Forest for the Fire on the Mountain 50K and 25K races. The event features technical trails, forest roads, and strict cutoff times. It's scheduled for November 1, 2026, with a training run o..

This trail run in Germantown, MD takes place on November 7, 2026, starting from the scenic Button Farm. Runners can choose from a half marathon, 10K, or 5K course on the singletrack trails of Schaeffer Farms. Virtual race options are also a..

Experience a 50 mile trail run through the forested rolling terrain of the Seneca Greenway and Muddy Branch trails in Maryland featuring single track dirt paths and natural stream crossings.

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.

This Fall Backyard Burn trail run takes place in the scenic Hemlock Overlook park along Bull Run. Runners can choose between a 5-mile or 10-mile course on trails and dirt roads, with good spectator areas. The event is part of a series and s..

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 Void is a 48 hour ultramarathon run entirely inside a dark, abandoned tunnel in Pennsylvania. Runners complete 63 out and back laps totaling 160 miles with no scenery and limited support access. Entry is by application, prioritizing exp..

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..

Run the Fall Backyard Burn trail race at scenic Riverbend Park in Great Falls. Choose between a 5-mile or 10-mile course along the Potomac River. Enjoy riverside singletrack, a family-friendly kids' race, and a post-race breakfast.

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..

A community cross country event in Catonsville on Thanksgiving offering a chip timed 1 Mile Family Fun Run and a 5K. All proceeds support the CHS Cross Country program and awards include cash and age group prizes.

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..

This trail run explores the scenic paths of Fountainhead Regional Park along the Occoquan Reservoir. Choose from a 5-mile or 10-mile course on a mix of hiking trails and old dirt roads. It's part of a series and supports a local charity, Ho..