Trail Running calendar near Dewey Beach 2026-2027

A trail 25k in Queen Anne, Maryland on November 21, 2026. Mostly single track with runnable hills, three aid stations, food options, and awards for the top three men and women.

A trail 5K at Autumn Lake Winery in Williamstown, NJ on Thanksgiving morning with dirt, grass, and sand underfoot. Awards for the top three male and female finishers, free entry for kids 14 and under, and a portion of proceeds support Lucky..

A cross country style 3 miles race at Anthony Campanella Park in Vineland, NJ, welcoming runners and walkers of varying ages. Awards for top overall finishers and multiple age groups; online registration with several payment options.

Join the 28th annual Reindeer Stampede 5k at Killens Pond State Park for a run or competitive walk. This established event supports local cross country and features festive awards and a post race party with seasonal treats.

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.

A trail 5K on February 20, 2027 at the Wicomico Ranger Station in Parsonsburg, MD that raises funds for 4STEPS therapeutic riding programs, with age/gender prizes in Amazon gift cards and a $32 registration fee.