Trail Running calendar near Lewes 2026-2027

A fall trail event at Trap Pond State Park featuring a 4.5 mile loop on the Bob Trail and a 2 mile walk. Participant fees support Legacy Academy.

A 25K trail race in Queen Anne, MD on November 21, 2026 with mostly single-track trails, three stocked aid stations, awards for top three men and women, and organization by Algonquin Ultras and the Centreville Crushers.

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.

A community 5k run/walk and a separate competitive walking 5k at Killens Pond State Park on November 28, 2026. The event supports Milford High School Cross Country and features chip timing, awards, shirts, and post race refreshments.

An eight hour endurance run at Terrapin Nature Park where participants complete 2.8 mile laps to earn surprises placed in a personal stocking. Awards are given to the male and female with the most laps.

Experience a fast and flat end of year ultra at Cooper River Park. Run a paved 3.75 mile loop featuring views of the Philadelphia skyline and access to a fully stocked aid station throughout the day.

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.

A spring trail 50K at Susquehanna State Park with two identical loops, about 4,300 feet of climbing and several stream crossings, supported by aid stations and volunteers.

A reborn six day track ultrarunning event at Cooper River Park offering timed events from six hours up to 144 hours.

A turtle themed 5K at Hopkins Farm Brewery in Havre De Grace raising funds and awareness for the Susquehannock Wildlife Society. The trail race includes wooden participant medals, costume prizes, and an after party with live music.

A multi-distance event in Lewes, Delaware with 5K, 10K and half marathon options plus race walk and heavy march categories. The weekend includes an educational exhibit, vendors and live music while supporting wounded warriors and homeless v..

A morning **5K** held as part of the Fair Hill Scottish Games on May 15, 2027, in Elkton, MD, with on-field entries accepted, an entry fee that includes admission, and cash prizes plus trophies for top finishers.