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Armchair Adventures: Ghosts and Graves of Sleepy Hollow

Sleepy Hollow, NY
Scary Jack O'Lantern from Sleep Hollow, New York during Halloween.

By Evelyn B. Kelly, PhD 

October in Sleepy Hollow, New York is “the most wonderful time of the year.” There are blazing Jack-o-lanterns, exciting street fairs, and yards decorated with a kaleidoscope of reds, greens, and yellows. We are approaching Sleepy Hollow from Tarrytown, NY along Route 9. Buried under the black asphalt is the dirt road supposedly traversed by Ichabod Crane and the Headless Horseman, made famous by the writer Washington Irving in the “The Legend of Sleepy Hollow.” 

I creep along as part of the crowd, haunted by my thoughts of the headless horseman riding past this ghostly oak tree; all of New York must have emptied into this small valley. Despite the mob, I want to find the past in the present and concentrate on the spirit and history of this interesting Dutch colony. 

History of Sleepy Hollow

It all began in 1609 when the Dutch East India Company hired explorer Henry Hudson, who found and named a magnificent river and made way for colonies of Dutch people to lay down family roots in 1658. The settlers were energetic trappers and farmers who pioneered free trade and tolerance. They also brought a wealth of tales – including their ghost stories – with them. In fact, the area is considered one of the most haunted places in the U.S. 

Washington Irving inspired the renaming of the village of Sleepy Hollow (until 1996, it was called North Tarrytown). He moved to the area in 1798 to avoid the outbreaks of yellow fever. He was introduced to local ghost stories, including a tale of a Hessian soldier, a mercenary for the British, whose head was shot off by a Continental Army cannon. The moral of his story: Do not let superstition guide your actions and overwhelm your reason. From the crowds here, it does appear that his intent is hidden in the hoopla. 

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Gravestones and Glowing Ghost Ships

When I was a kid, someone once told me that whenever you pass a cemetery, hold your breath so you will not breathe in evil spirits. My maxim is tested as our guide led us to the old Dutch church and its churchyard prominently mentioned in the legend. The ghost rides in a nightly quest of his head, hurrying to get back to his grave before daybreak. The two-acre churchyard is the resting place of settlers like those that inspired Katrina Van Tassel and Brom Bones.  

Bureau of Engraving and Printing – U.S. Post Office, Public Domain

The 90-acre Sleepy Hollow Cemetery, on the other hand, has unique headstones, magnificent mausoleums, twisting narrow roads, and over 45,000 gravesites. Washington Irving himself is buried here along with Andrew Carnegie, Walter Chrysler, Elizabeth Arden, Brooke Astor, and William Rockefeller. It is heavily wooded with cedars, sycamores, and oaks. 

Ghosts are not only on land, but in the water. An area where the river widens is called Tappan Zee: “Tappan” for the native tribe that lived in the region and “Zee,” the Dutch word for sea. The glowing ghost ship – The Flying Dutchman – has been sighted in the Hudson; it appears during a turbulent storm and then disappears. 

Even with the crowds I was alone in my own thoughts, reflecting on the names on the tombstones and periodically reminded of these great people. However, it was satisfying seeing the crowds having fun and enjoying themselves. I realized that this was not only a sleepy tourist destination but was a wide-awake land of history and peace, a place of celebration of life and joy.