Trail Running Calendar Maryland 2026-2027

The Pemberton 24 is a unique 24-hour challenge in Maryland's Pemberton Park. Runners and teams attempt to complete as many hourly 5 km loops as possible, earning points for each one. It's a test of endurance with a supportive camp atmospher..

Event Information The River's Edge Endurance Challenge takes place in Brunswick, Maryland. The event is the 8th annual edition and offers three different race distances. Distances 5K (3.1 miles) 3 Hour Endurance Race 6 Hour Endurance Chall..

This community 5K run/walk takes place on a wide natural trail at the Agricultural History Farm Park. The event includes a pre-race pep rally, post-race snacks, and awards for top finishers.

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.

The Rocky Gap Trail Run features a 25K and 50K course through the scenic loops of Rocky Gap State Park. Runners can participate solo or in relay teams of 2 or 3. The event includes a base camp aid station and on-course support.

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 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.

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..

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.

Event Overview The PHUNT 25K/50K Trail Race takes place on Saturday, January 16, 2027, at the Fair Hill Natural Resource Management Area in Elkton, Maryland. The start and finish location is the Edward L. Walls Activity Hall at the intersec..

The 4Steps Therapeutic Riding 5k will take place in Parsonsburg on Saturday 20 February 2027. You can run 5 kilometers.