First offered by Chicago Yacht Club in 1915 to encourage competition between the club and eastern yacht clubs.
The first club to accept the challenge was Indian Harbor Yacht Club of Greenwich, CT. Addison Hahan skippered the P Class yacht Josephine to victory for IHYC and the cup went to Greenwich. In 1946, at the suggestion of IHYC, the competition was reinstated using Luders L-16’s and continued for eight years.
In 2014 the event was restarted in Shields. The 2014 event was held in Lake Michigan (Chicago, IL) was won by the Monterey Yacht Club (Shields Fleet #7). The 2015 event was held in the Pacific Ocean (Monterey, CA) and won my the Beverly Yacht Club (Shields Fleet #10). The 2016 event was held in Marion, Massachusette on Buzzards Bay (Atlantic Ocean) and won my the Beverly Yacht Club (Shields Fleet #10).
The 2017 event is scheduled for June 23 to 25, 2017 in Larchmont, New York.
See Chicago Yacht Club web page, list of winners (1915 to 1953) and list of winners (2014 to 2016).