Trail Running calendar near Chester 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.

An annual Roxbury Road Runners charity race held on Thanksgiving Day, with proceeds supporting the Roxbury Scholarship Foundation and the Roxbury Ambulance Association. Results for the race are published as part of the club series.

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 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 trail running event at Sleeping Giant State Park on December 5, 2026, using the park's varied trails and scenic viewpoints. Organized by Steep Endurance with entry fees listed between 50 and 80 USD.

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.

A 5K trail run and free kiddie fun run at Bethpage State Park with a virtual option, a good luck clover shirt for participants, and post race refreshments including beer for those 21 and over.

Trail races at Sleeping Giant Park in Hamden, CT offering a 25K loop with 3K+ vertical and a 50K two loop option. The course features technical singletrack, steep rock scrambles, aid stations, and finisher medals.