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Although the area was originally home to the Weckquaesgeek Indians, the histories of Sleepy Hollow and Tarrytown did not begin until the late 1600s with the arrival of wealthy Dutch businessman Frederick Philipse. Philipse was given permission to purchase large tracts of land along the Hudson River’s eastern shore. He ultimately acquired around 90,000 acres of land and set to building his manor house, the Old Dutch Church of Sleepy Hollow and a gristmill.

During the 18th century, much of community life revolved around the gristmill, but there were a few farms and small shops that were also established in the area. Though the village was located on “The Neutral Ground,” a hotly contested no-man’s-land during the American Revolution, it was the site of one very important event. It was in Tarrytown that a British spy, Major John Andre, was captured with papers outlining a plot to surrender West Point to the British army – which was given to him by Benedict Arnold. Three local militiamen – John Paulding, Isaac Van Wart and David Williams – caught Andre and exposed the plot on September 23, 1780.

The arrival of another important figure in the late 1790s would put the area on the map for centuries to come. Author Washington Irving spent time hunting, fishing and socializing in the community with friend and relative James Paulding. Later, Irving would immortalize the community in his tale, The Legend of Sleepy Hollow – depicting the local landscapes and structures (notably the Old Dutch Church and burying ground, which served as an important setting in the short story).

The 19th century brought on new growth, and in 1874 Sleepy Hollow incorporated as a village under the name North Tarrytown, until its renaming in 1996. At the turn of the century, Tarrytown and Sleepy Hollow began attracting new businesses and wealthy families, who began building sprawling castle-mansions. As a result, the area of Sleepy Hollow and Tarrytown became known as a “millionaire’s colony.”

Today, Tarrytown stands as a town of approximately 11,500, Sleepy Hollow at about 9,000. The villages have worked to ensure that the history of this charming area remains preserved. The Historical Society of Sleepy Hollow & Tarrytown maintains a museum packed with local artifacts, pictures and documents from the 1600s to the present day. In addition, Historic Hudson Valley (HHV) oversees several of the Hudson River Valley’s major historic attractions, such as Washington Irving’s Sunnyside estate, the Philipse family’s Philipsburg Manor and the beautiful Union Church of Pocantico Hills, while the National Trust for Historic Preservation maintains the Lyndhurst estate and the Rockefeller family’s Kykuit estate (though, HHV operates Kykuit’s tour program).

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