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Cannondale is a census-designated place (CDP) within the town of Wilton in Fairfield County, Connecticut, United States. As of the 2020 census, Cannondale had a population of 396. The neighborhood consists of many old homes on large, almost rural lots now largely wooded. The English first settled the land in the 17th century. At the center of Cannondale is Cannon Crossing, a small shopping village of boutiques and restaurants made up of 19th-century buildings restored by actress June Havoc in the late 1970s on the east side of Cannondale Railroad Station. Both are part of Cannondale Historic District, which encompasses the central part of Cannondale and most of its significant historical buildings.