Trail Running calendar near Waterbury 2026-2027

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.

A 5K trail run and free kiddie run at Bethpage State Park that starts on a polo field and moves onto soft, scenic trails. Virtual entries are accepted and donations support the Never Stop Running Foundation.

A 123 mile point to point ultramarathon across Connecticut featuring about 57 miles of trail, a 36 hour cutoff, solo and relay options, and belt buckles for 200K finishers.

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.