Trail Running calendar near Chesapeake City 2025-2026

We have found 51 Trailruns within 80 miles of Chesapeake City. See below where and when you can find the races.

The Run Like a Mother 5K Trail Race and 1 Mile Fun Run, hosted by More Kids on Bikes, is a family-friendly event aimed at promoting an active lifestyle and celebrating mothers. Scheduled for May 11, 2025, at Yeager's Farm & Market in Phoenixville, PA, the event features a scenic 5K trail race and a..

The Conestoga Crusher 10K Trail Race, along with the Conestoga Cruiser 5K Trail Race and a Kids Trail Race, is scheduled for May 17, 2025, in Holtwood, PA. The event offers scenic trail running through Kelly's Run Nature Preserve, featuring creek crossings, steep climbs, and beautiful views from the..

The Patriot Power 5K is a charitable running event held on May 17, 2025, in Reading, Pennsylvania, with a virtual participation option. Organized to honor and support military veterans, the race benefits Team RWB, an organization dedicated to enriching veterans' lives through social and physical act..

The Coventry Woods 5K & 10K Trail Challenge is an exciting trail running event taking place in Pottstown, Pennsylvania. Scheduled for May 18, 2025, this race features two distances: a 5K and a 10K, both set on scenic trails that include a mix of rocky terrain, roots, and various track types. Partici..

The First State Trail Race, taking place in Wilmington, DE, offers a scenic and challenging experience for runners of all levels. Set in the picturesque Brandywine Creek State Park and First State National Historical Park, participants can choose from three distances: a 10K, 25K, or 50K. Each course..

The Charlie Horse Trail Half-Marathon and Dirty Pony 5K are annual running events held in Mohnton, PA, benefiting Berks Co. Special Olympics. The half-marathon features a challenging course combining trail, road, and adventure elements along the Horse-Shoe Trail, with scenic sections, aid stations,..

June 2025

The Dash and Deciduous 5K Trail Run is a unique and challenging event taking place at Crystal Lake Park in Bordentown, NJ. Scheduled for June 7, 2025, this free, timed "FATASS" run is designed for a limited field of 40 runners, emphasizing a fun and competitive atmosphere. Participants can expect a..

The 1/2 Sauer 1/2 Kraut is a unique running event held at Pennypack Park in Philadelphia, PA, featuring a half marathon and marathon. The race takes place along a scenic, mostly shaded bike trail alongside Pennypack Creek, with a course described as a "rollercoaster" due to short, steep hills. Parti..

Smith’s Challenge Trail Run, organized by the Lancaster Road Runners Club, celebrates its 36th anniversary in 2025 as the oldest trail race in Central Pennsylvania. Held in Lancaster County Central Park, the event features 5-mile and 10-mile trail races that traverse challenging courses with trails,..

The Run For the Ages 10K Trail Chase is a scenic trail running event held in Nolde Forest, Cumru Township, near Reading, Pennsylvania. This unique race features an age-graded start, giving runners of all ages and genders a fair chance to compete for the overall title. The course is a well-marked 10K..

The Blue Crab Bolt Trail Run at Seneca Creek State Park in Gaithersburg, MD, is the opening race of the 14th annual Blue Crab Bolt Trail Running Series. Scheduled for June 21, 2025, it offers two trail race distances: approximately 5K (3.3 miles) with 200 feet elevation gain and 10K (6.4 miles) with..

The Reckless Red Eye Endurance Run is an exciting endurance event scheduled for June 22, 2025, in Columbus, NJ. Participants can choose from various race formats, including 3-hour, 6-hour, 12-hour, and a 12-hour team relay. The course features a flat and fast 3.3-mile loop at the Burlington County F..

The 23rd Dewey Beach Patrol 5k is a road race held in Dewey Beach, Delaware, starting at North Beach Restaurant on McKinley Street. This USATF-certified out-and-back course runs through residential neighborhoods, offering a scenic and competitive environment. The event includes a 5k run/walk and a c..

On The Rocks Trail Runs is an exciting trail running event taking place at Rocky Ridge County Park in York, PA, featuring multiple race distances: 50K, 33.3K, 16.7K, and 10K. The course is characterized by rolling hills, rocky terrain, and tree roots, providing a challenging experience for participa..

July 2025

The Sweet Air Trail Race, organized by the Baltimore Road Runners Club, is a challenging 7 to 8-mile trail run held at Gunpowder State Park in Sweet Air, Maryland. The course features a mix of rolling hills, fast sections, water crossings, and occasional mud, providing a varied and adventurous runni..

The Endless Summer 6-Hour Run is an annual endurance event held in Annapolis, Maryland, organized by the Annapolis Striders. Participants run for six hours on a 2.5-mile loop course that offers scenic views of Chesapeake Bay and the Bay Bridge. The event supports the Semper Fi Fund, with a portion o..

The Murderkill Ultramarathon is an exciting running event held at Killen's Pond State Park in Felton, Delaware. Participants can choose from three race options: a 50-mile, a 50K, or a 12-hour challenge, all set on a scenic 3.1-mile dirt loop trail. The course features a mix of shaded paths and gentl..

The Run the Vineyards Bohemia Manor Farm 8K is an exciting running event set in the picturesque Bohemia Manor Farm in Chesapeake City, MD. Participants can choose between a scenic 8K trail run and a 5K run, both featuring beautiful views of vineyards and the Bohemia River. The event includes chip-ti..

August 2025

Loopy Looper is an ultra running event held at Cooper River Park in Pennsauken, New Jersey, featuring a fast and mostly flat 3.75-mile paved loop with scenic views of the Philadelphia skyline and river. The race offers multiple distances including 12-hour, 24-hour, and a 101.25-mile ultra, as well a..

The MD Heat Trail Race, held in Elkridge, Maryland at the Patapsco Pickall Area, offers challenging trail running options of 25K and 50K distances. The course features rolling single-track trails with over 2,000 feet of elevation gain, including technical rocky sections, two river crossings, and a s..