To be fair, the whole “Long Island is not an island despite being an island” thing came about for rational reasons. As the 1985 United States v. Maine case reads, the Supreme Court had to get ridiculously specific about which areas of water belonged to which state. Block Island and the Block Island Sound seemed to be particular sticking points, as they more or less occupy the intersection of New York, Connecticut, and Rhode Island — if you draw lines out from their coasts.
Just to illustrate how detailed the Supreme Court got, here’s its (i.e., the United States’) position: “The coast of the State of Rhode Island, except as to Block Island, is the ordinary low water line along the mainland beginning at the Massachusetts border to a point off Sakonnet Point, then a straight closing line across Narragansett Bay to Point Judith, then the ordinary low water line along the mainland to the Connecticut border. As to Block Island, the coast of the State of Rhode Island is the ordinary low water line around Block Island.”
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Demarcating what water belongs to which state also related to boat licensing and a dispute between Connecticut and Rhode Island. Specifically, Rhode Island heavy-handedly required every registered “foreign vessel and every American vessel” that passed through Block Island Sound to have a pilot on board dispatched from the Rhode Island State Pilotage Commission — an organization designed to keep boaters navigating correctly.
