Trail Running Calendar Maryland 2026-2027

An out-and-back 3.8 mile run at Pen Mar Park with about 1.8 miles of ascent to High Rock Overlook. Held August 30, 2026, with registration deadlines and a higher fee on race day.

A 24-hour event in Salisbury where individuals and four-person teams run hourly 5K loops on Pemberton Park trails. Points-based scoring, an aid station at start/finish, and awards for top individuals and teams.

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..

Join a community 5K run and walk through the scenic trails of Agricultural History Farm Park. Enjoy a morning of music and fitness with events for all ages and awards for top finishers.

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 beauty of Western Maryland at Rocky Gap State Park with 25K and 50K trail races. Run solo or join a relay team to navigate three distinct loops featuring scenic lake views and ridge traverses.

A trail-based community event on October 11, 2026 at Bretton Woods Recreation Center featuring a 5K run and 1 mile walk to support the Michael Long Memorial Fund and addiction prevention and recovery services.

Boulder Dash at Pinesburg Quarry takes place October 17, 2026 in Williamsport, MD and includes a 5 Mile race, a 5K, and a 1 Mile fun run. Registration opens May 1, 2026 and the quarry will not be operational during the event.

A scenic, well-marked trail event in Patapsco Valley State Park offering in-person and virtual 50k and 25k options, Brooks shirts, five aid stations, and distinct finishers awards for each distance.

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

Fire on the Mountain in Little Orleans, Maryland, on November 1, 2026, offers a 50K and a 25K on forest trails and service roads in Green Ridge State Forest. Both courses include multiple aid stations and official cutoff times.

Trail races at Button Farm in Germantown, MD on November 7, 2026 feature twisty singletrack and open farm fields, with distances of 13.5, 6.7 and 3.2 miles. The event includes aid stations, portajons, finisher medals and post-race food.

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.

A looped trail race at Rosaryville State Park offering 50K and 20K courses through wooded single track and meadows, with two aid stations, drop bag access, participant limits, and time limits for each distance.

The Tuckahoe 25k in Queen Anne, MD on November 21, 2026 is a 25 kilometer trail race featuring mostly single track, runnable hills, and some muddy sections. Three stocked aid stations support runners and awards go to the top three men and w..

A 5K and 10K held at Carderock Park along the Chesapeake and Ohio Canal Towpath on November 22, 2026, with a flat, fast trail, walkers welcome, and virtual entry options that include medals and shirts.

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.

A roughly 10 mile trail and canal run near Great Falls on November 26, 2026. Entry opens November 12 and is limited to 29 runners, and participants are responsible for their own medical care.

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.