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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