Trail Running calendar near Chesapeake City 2025-2026

The 27th Milford Cross Country Booster Reindeer Stampede 5k is a festive running event held at Killens Pond State Park in Felton, Delaware. This 5k run/walk features chip timing with MYLAPS BibTag and offers competitive walking and running categories. Participants receive long sleeve tee shirts and..

The Tame the Tower Trail Challenge is a trail running event held in Mt. Gretna, Lebanon, Pennsylvania, at Clarence Schock Memorial Park. Scheduled for December 13, 2025, it features two distances: a 10-mile "T-Rex" and a 5-mile "Ferocious" run.The courses are marked with colored flags—pink for the 1..

The Frosty Looper 8-Hour is an ultrarunning event held at Cooper River Park in Pennsauken, NJ. Participants run as many laps as possible on a fast, flat 3.75-mile paved loop around the river, featuring scenic views of the Philadelphia skyline and water. The course includes mostly flat terrain with s..

Naked Nick is a trail running event held in Leesport, Pennsylvania, featuring 25K and 50K distances around Blue Marsh Lake. The course is a lollipop-shaped route on the lake's south side, combining 80% single-track trails and 20% gravel roads, with moderate elevation gains of approximately 1,500 fee..

The Mid-Maryland Trail Festival 50k is a 31-mile ultramarathon held at Rockburn Branch Park in Elkridge, Maryland. The course consists of six loops, each approximately 5.179 miles, winding through wooded trails. Participants can run the full 50k solo or form relay teams of 2 to 6 members, exchanging..

The Naked Bavarian is an affordable ultra trail running event held at Blue Marsh Lake in Leesport, Pennsylvania. Offering 20- and 40-mile distances, the course features a lollipop loop with mostly runnable trails—80% single track and 20% gravel roads—covering approximately 2,000 feet of elevation fo..

The Genesee Valley Ultra is an endurance running event held at the Genesee Valley Outdoor Learning Center in Parkton, Maryland. It features a 2.5-mile trail loop through farm roads, grass fields, and some double track on private property. Participants can choose from 6, 12, or 24-hour race durations..

The Rockland Rad Run is a trail running event held at Forever Farm in Mertztown, Pennsylvania, featuring a half marathon, 10k, and 5k distances. Set amidst the scenic Pennsylvania woods, the course offers a challenging experience through rolling, rugged terrain, ideal for trail running enthusiasts...

The Matzah Miles 5k Trail Run and 1 Mile Family Walk is a festive event celebrating Passover, set to take place in Medford, NJ. Participants can choose between a competitive 5K trail run, a leisurely 1-mile family walk, or a fun 50-yard Kids Dash. The event features a pre-race warm-up, games for chi..

The Breeze Thru The Trees 5k is a cross-country running event held at Ruppert Nurseries, a 500-acre tree farm located in Gaithersburg, Maryland, within Montgomery County’s Agricultural Reserve. The event features a 5K run and a 1-mile fun run, offering participants a scenic course winding through a..

Run to Remember in Sykesville, MD, is a memorial running event held at Piney Run Park featuring distances of 50K, 25K, 5 miles, and an 8-hour challenge. The course is a scenic 5.25-mile loop through woods and meadows, with about half the route offering lake views. Runners complete multiple loops dep..

The Farm Park Challenge is a unique trail running event hosted by My Muddy Shoes at the Agricultural History Farm Park in Montgomery County, Maryland. Participants can choose from three timed challenges—3-hour, 6-hour, or 10-hour—where runners must complete one lap of the course each hour, resting o..

The Race4Warriors Half Marathon is part of a multi-distance event held in Lewes, Delaware, featuring 5K, 10K, and Half Marathon challenges. The race supports Wounded Warriors and Homeless Veterans, aiming to unite military and civilian communities. The USATF-certified course starts and finishes at A..