Trail Running calendar near Charlestown 2026-2027

The Tom Centinaro Memorial "Dam" Race will take place in Waterbury on Saturday 17 October 2026. You can run 4 miles.

Join the Womp Romp at Wompatuck State Park for muddy, scenic trail loops through South Field with 10 Miler and 50K options and hearty aid stations. Proceeds support local charities for a fun, community focused fall run.

The Grills Trail Run will take place in Misquamicut on Saturday 24 October 2026. You can run between 10 and 10 miles.

Enjoy scenic trails around Watchaug Pond at the Li'l Rhody Runaround on November 15, 2026, with 8 mile and 4 mile course options. Part of the WTAC Fall Trail Race Series, it welcomes runners of all levels.

A trail half marathon in Roosevelt Forest, Stratford, run as eight laps of a 1.64 mile wooded loop with roots, rocks and rolling hills. The event features a children’s book drive, costume prizes, a finisher medallion and on-course aid.

Join the Soul n Body Thanksgiving Trail Run in Wolcott CT for a spirited 3.5 mile loop around Mill Pond Way, complete with finisher medals, swag and post race yoga. Proceeds benefit endometriosis research and furry friends are welcome.

A 5K trail run through Roosevelt Forest in Stratford, CT on December 19, 2026, with awards for the top three men and women and a custom finisher medallion. A portion of proceeds supports local charities.