The Centerport Yacht Club hosts two premier Performance Handicap Racing Fleet (PHRF) challenges – The Winkle Cup, which was organized in 1955 and is currently run in cooperation with Lloyd Harbor Yacht Club's Katrina Cup; and The William K. Vanderbilt II Memorial Cup, which was organized in 1981 in conjunction with the Vanderbilt Museum.
CYC also hosts The Commodore's Cup race and The Cruising Canvas Cup race, which are members-only events.
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