Trail Running calendar near Brookfield 2026-2027

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.

Trail 5K in Roosevelt Forest, Stratford CT on Dec 19, 2026. Participants can run, jog, hike or walk and may wear holiday costumes; awards go to the three fastest men and women and a portion of proceeds supports local causes.