Halloween wouldn’t be Halloween without at least giving a nod and a drive-by to Tarrytown and Sleepy Hollow – the location being the inspiration for Washington Irving’s famous tale “The Legend of Sleepy Hollow.” Although part of different townships, Tarrytown and Sleepy Hollow are closely associated both geographically and by history.
Washington Irving’s Estate, Sunnyside is located in Tarrytown, while Philipsburg Manor, the Old Dutch Church, Sleepy Hollow Cemetery and the Headless Horseman Bridge are located in Sleepy Hollow. An 18-foot statue of Ichabod Crane being chased by the Headless Horseman was erected in Sleepy Hollow on Halloween morning 2006. So the statue will celebrate its first birthday this Halloween.
“The Legend of Sleepy Hollow, a short story written Washington Irving was first published in Birmingham England in 1820 under the same cover with “Rip Van Winkle.”
The story is revolves around a schoolmaster, Ichabod Crane, who competes for the hand of Katrina Van Tassel , the daughter of a wealthy farmer. Upon leaving the Van Tassel home one autumn night, Crane finds himself being chased by a “headless horseman” – the ghost of a mercenary soldier of the revolutionary war – who rides at night in search of his lost head. Ichabod Crane disappears after crossing the headless horseman bridge – heading past the cemetery. He was never to be seen again. The sight of the bridge is located right next to the Old Dutch Church and cemetery.
In memory of the famous Washington Irving Tale Philipsburg Manor hosts an event at Halloween where the headless horseman rides again. It’s a great family outing complete with gallows, ghosts, goblins, lanterns, bonfires and one headless horseman. The public can stroll through the property at their own pace and enjoy the sights.
Some more trivia: Here is an abbreviated list of the Sleepy Hollow Cemetery’s more celebrated interred occupants.
Frederick Philipse
Washington Irving
Vincent Astor
Elizabeth Arden
Andrew Carnegie
Walter Chrysler
Samuel Gompers
Mark Hellinger
Harry and Leona Helmsley
William Rockefeller
For more information about the historic sights near Tarrytown and Sleepy Hollow click here.

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