Trail Running calendar near Darien 2026-2027

Celebrate the holiday at the Inwood Hill Turkey Trot 5K Run and Walk. This event offers a scenic course through Inwood Hill for participants of all abilities to enjoy a morning of fitness and community.

A looped trail party at South Mountain Reservation in West Orange NJ offering 5K, 10K, 25K, 50K and a kids 1 mile on a mixed carriage road and singletrack course with onsite aid and a charity partnership.

Enjoy a post holiday run or walk through the scenic trails of Bethpage State Park. Participants earn themed swag and enjoy refreshments from local partners at this festive 5K event.

Experience a 5K trail race through the scenic Stillwell Woods Preserve in Woodbury. This event honors the memory of Rob Lauterborn and supports the Center for Developmental Disabilities.

Experience a unique 5K trail run at Belmont Lake State Park where the focus is on luck rather than speed. Enjoy a chance to win cash prizes and refreshments at the finish line during this late November event.

A looped trail race at Holmdel Park with a 50K (ish) and a Halfish option on ~4.65 mile laps, varied trail terrain, RFID lap timing, and an 8 hour cutoff. Proceeds support MissionCleanWater.

A 5K trail event through Roosevelt Forest in Stratford, CT on Dec 19, 2026, open to runners, joggers and walkers. Holiday costumes are allowed, awards recognize the fastest three men and women, and proceeds benefit local organizations.

Join this unique mystery trail run in Edison featuring five mile and two mile options through wooded terrain. Enjoy a non competitive atmosphere with a secret start location and a post run social gathering for participants over 21.