Sail to the Finish 2M Run

Lace up your running shoes and set your sights on the finish line at the 4th Annual Sail to the Finish 2M Run, taking place on Saturday, May 2, 2026, in picturesque Middlebury, CT. This engaging 2-mile road race offers a unique out-and-back course, beginning and ending at the Quassapaug Sailing Center. Runners can anticipate a refreshing downhill start for the first mile before taking on a manageable uphill challenge on the return, described as "not that steep." Typical race day conditions in early May feature comfortable highs around 67F and lows around 44F, with a modest 14% chance of precipitation, creating ideal running weather.

Beyond the scenic course, this event is a heartfelt fundraiser for the Quassapaug Sailing Center, a non-profit dedicated to providing sailing instruction and fostering a love for water sports in children, including offering vital scholarships. This race truly stands out as a vibrant community gathering. Adding to the festive atmosphere, May 2nd, 2026, marks International Harry Potter Day, and participants are encouraged to embrace the magic by coming in costume for a chance to win awards.

Due to limited space, entries for this popular event are expected to sell out quickly, so early registration is highly recommended to secure your spot. Awards will be presented to overall male and female finishers, as well as the top three in various age categories from 19 and under to 70 and up. Remember that parking is limited at the Quassapaug Sailing Center (30 West Lake Road, Middlebury, CT 06762), so carpooling is encouraged to ensure a smooth start to your race day adventure.