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Memoirs of a Dockmaster
The harbor is one of the Pines’ most distinctive features. In the late 1980s it was its own kind of theater-- a floating stage where yachts, ferries, and seaplanes carried an ever-changing cast of characters, ranging from celebrities like Madonna, Peter Allen, and Liza Minnelli to foreign dignitaries guarded by men with Uzis to hundreds of drag queens arriving in full regalia for the July 4th Invasion. Henderson Rose was a dockmaster from 1986 to 1990 and had a front row seat to it all. From chatting with Tony Randall on the docks to sipping cocktails with Joan Rivers and helping to keep order as throngs of revelers flowed between Tea, house parties, and the Pavilion, his memories of those summers are as fresh as if they happened yesterday.
The Annual Labor Day Drag Party (aka The Fools Paradise Drag Party) Est. 1996
The Labor Day Drag Party is a long-standing tradition in Fire Island Pines that holds a Guinness World Record for having the most Madonna impersonators in a single place. It is a stunning example of over the top glamor and fabulousness, done in a way that defies convention, that the Pines has come to represent.
Fire Island Celebrity history- Madonna
1989. The end of the 80’s brings Madonna to Fire Island Pines to visit her brother Christopher Ciccone. She brings some friends along for the ride…

