4th Annual Sail to the Finish 2M Run

Lace up your running shoes for the 4th Annual Sail to the Finish 2M Run, taking place on Saturday, May 2, 2026, in the picturesque town of Middlebury, CT. This engaging 2-mile event offers runners a unique out-and-back road course, beginning and ending at the scenic Quassapaug Sailing Center. The race starts with a rewarding downhill first mile, providing a swift beginning before you tackle the gentle uphill return to the finish—a climb described as "not too steep," ensuring a satisfying challenge without being overly arduous.

Beyond the invigorating course, the Sail to the Finish Run is a fantastic opportunity to support a great cause: the Quassapaug Sailing Center. This non-profit organization is dedicated to providing sailing instruction, fostering a love for water sports, and offering scholarships to children in need. Typical race day conditions in early May feature comfortable highs around 67°F and lows around 44°F, with only a 14% chance of precipitation, promising ideal running weather. As this popular event has limited entries and often sells out, early registration is highly encouraged.

Adding a touch of whimsical fun, the race day coincides with International Harry Potter Day! Participants are encouraged to come dressed in their best Harry Potter costumes for a chance to win awards. Prizes will also be given to the overall male and female finishers, as well as the top three in various age categories. While parking is limited at the Quassapaug Sailing Center, carpooling is encouraged to enhance the community atmosphere. Join fellow runners for a day of community, camaraderie, and a shared love for the outdoors, all while contributing to a worthy cause.