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The writer Washington Irving described Tarrytown in "The Legend of Sleepy Hollow" (1820). Irving began his story, "In the bosom of one of those spacious coves which indent the eastern shore of the Hudson, at that broad expansion of the river denominated by the ancient Dutch navigators of the Tappan Zee, and where they always prudently shortened sail and implored the protection of St. Nicholas when they crossed, there lies a small market town or rural port which by some is called Greenburgh, but which is more generally and properly known by the name of Tarry Town. This name was given, we are told, in former days, by the good housewives of the adjacent country, from the inveterate propensity of their husbands to linger about the village tavern on market days." The Underground Railroad ran through Tarrytown prior to the end of the U.S. Civil War.
Tarrytown later became a favorite residence for many rich New Yorkers, including John D. Rockefeller, who first moved to Tarrytown in 1893. Kykuit, Rockefeller's elaborate mansion, was completed in 1906. In 1914, Kykuit became the site of numerous labor protests by radical anarchists, which protests were broken up by police in a series of violent clashes. Kykuit was the intended target of at least two bombing attacks planned by anarchists associated with the radical journalists Alexander Berkman and Luigi Galleani.