On a winter evening in 1930, five volunteer firemen from Freeport’s Truck Company No. 1 of the old Extension Hook and Ladder Company gathered for their usual lively conversation, accompanied by a bottle of gin and some Limburger cheese. As most of them owned small boats, the discussion naturally turned to boating and the enjoyable days they spent cruising and fishing in the creeks and bays around Freeport and neighboring towns. Someone eventually proposed an ambitious idea: “Why don’t we get together next summer and cruise to Shelter Island?” At the time, this was no small feat. There were no Jones Beach Tower landmarks, no state channels, and no channel markers. Navigation relied on scattered saplings or sticks placed by baymen and clam diggers—signs understood only by those in the know. Finding deep water required instinct and experience. After some discussion, they agreed that local baymen would need to be involved to ensure the boats could safely reach Shelter Island and return without running aground on sandbars. That’s when someone suggested, “If we’re bringing others along anyway, why don’t we start a yacht club?” With that simple idea, the Freeport Yacht Club was born. The five firemen who became the charter members were Louis Streck, the club’s first Commodore, along with Henry Von Elm, Charles A. P. Smith, Ward Frost, and Lewis Charles. Louis Streck also designed the club’s burgee, incorporating the Maltese Cross—an emblem of Truck Company No. 1 of the Freeport Fire Department—into its design.