Trail Running calendar near Stamford 2026-2027

The FEAR Trail Fest is a 5-mile trail race on the scenic Yellow Trail in New Jersey's Lewis Morris Park. With a runnable mix of rocks, roots, and climbs, it welcomes everyone from first-timers to veterans. The event focuses on sustainabilit..

A Thanksgiving morning trail run supporting endometriosis research. Choose a run or walk on the 3.5-mile Mill Pond Trail, followed by complimentary yoga. All participants get a finisher medal and swag bag.

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.

Experience a diverse 5K loop course at South Mountain Reservation featuring carriage trails and technical singletrack. Choose from distances ranging from a Kid's 1M to a 50K in this community focused trail event.

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.

The Tower Tag Challenge is a timed trail run in Connecticut's Sleeping Giant State Park. Runners complete 3.4-mile laps up and down the scenic Tower Trail within an 8-hour or 4-hour window. The event features awards, post-race refreshments,..

The Holmdel Classic is a December trail race in New Jersey's Holmdel Park, run on a challenging 4.65-mile loop. Participants can choose from three distances, with all proceeds supporting clean water projects worldwide. An eight-hour cutoff..

Experience an exclusive trail run through the scenic Roosevelt Forest in Stratford. This 5K event features a natural off-road course limited to a small group of participants and includes custom finisher medallions.

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.