Maidstone was founded in 1891 as a tennis and swimming club for wealthy summer residents. Three years later, in 1894, a rough three-hole course was created. This became a nine-hole course designed by the Scotsman Willie Tucker in 1896, and expanded to a full 18 in 1899 by Adrian Larkin, a member of the club. Willie Park, Jr. designed the 80-acre Gardiner Peninsula addition in 1922. The expansion resulted in the club having two 18-hole courses, but this was reduced to the current 27-hole layout by the Hurricane of 1938. The number of holes and their locations changed during the first half of the 20th century; now Maidstone contains 27 holes, with a nine-hole course used by the youngest and oldest members.
The Nine Course at the Maidstone Club facility plays to a 9-hole par-36 and maximum distance of 2,668. Designed by Willie Park, Jr., the Nine Course opened in 1922.
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