Wadawanuck Club was founded 1908 by a group of primarily Stonington summer residents. A small clubhouse and a tennis court were built on Water Street across from the present viaduct, and the club was named the Wadawanuck Tennis Club. Edward F. Darrell, Charles H. Simmons, J. Culbert Palmer, and Judge Gilbert C. Collins, the club’s first president, were among the founding members. In 1914 the club leased Nat’s Point at the head of the harbor from Elisabeth Palmer Loper, the granddaughter of Captain Nathaniel Palmer. The clubhouse was then moved to the Nat’s Point site and two tennis courts and a dock were added. Due to the popularity of one-design racing, the Wadawanuck Yacht Club division was established in the 1920s. Commodore Edward F. Darrell designed the club’s burgee of yellow and blue, echoing the sun and water. Racing in Scamps and Falcons, and later Lightnings, Blue Jays, Ensigns, and JY boats, has provided keen competition among members as well as with other yacht clubs around Fisher’s Island Sound.

The present clubhouse, designed by Herbert Simmons, opened in 1940 after the 1938 Hurricane destroyed all of the club’s facilities. New bathhouses and tennis courts soon followed. The Nat’s Point property was finally purchased in 1943, and the Darrell Boatyard at the eastern end was added in 1964. During the 1950s, the club began hiring lifeguards and program instructors to handle the post-war baby boom and new influx of members. In 2008, Wadawanuck Club proudly celebrated its 100th Anniversary.