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1.
A town located in Southern Westchester County. Home of Washington Irving and the Legend of Sleepy Hollow. Though surrounded by some wealthy neighborhoods, Tarrytown and Sleepy Hollow have more in common with the bigger cities of Westchester such as Yonkers, Mount Vernon, New Rochelle and White Plains. Cortlandt Street in Sleepy Hollow is equivalent to Warburton Avenue in Yonkers and other similar areas that you may find in the Bronx and Brooklyn. At it's closest point, Tarrytown is 10 minutes from Yonkers and about 16 minutes from the Bronx. To put it simply, it would take someone from Coney Island or Nassau County the same amount of time, if not longer to get to the heart of Manhattan.

Though located in a notoriously suburan county, the neighborhoods of Tarrytown and Sleepy Hollow are actually the last urban areas you'll see in lower New York until you reach Albany. Sleepy Hollow is just under the upstate border and rightfully so, considering it has nothing in common with the Northern portion of Westchester. In fact, Lower Westchester has more in common with the Bronx then it does with it's upper half. Let's not forget the Bronx used to be part of Westchester County in the early days.
Tarrytown and Sleepy Hollow are part of the county that SHOULD be the 5th borough of New York City. Take Southern Westchester and Northern Staten Island, throw 'em together and you got the illest 5th borough ever!
by Westchester's Finest December 05, 2005