(ODD)yssey, Blog Post

Did you know you can visit the real places from The Legend of Sleepy Hollow?

I have the perfect post for Halloween! My road-trip partner Sweetums has been writing a series of guest posts on places we would like to go, our Road Trip Bucket List. Enjoy … 

Painting of the Headless Horseman Bridge in Tarrytown, N.Y. , illustrating “The Legend of Sleepy Hollow.” (Wikimedia Commons)

This week’s entry on our weird roadtrip bucket list is closely associated with our current Halloween season. It is the small hamlet of Sleepy Hollow, New York the setting of the legendary ghost story The Legend of Sleepy Hollow which happens to be celebrating 200 years of publication.

“Another convulsive kick in the ribs, and old Gunpowder sprang upon the bridge; he thundered over the resounding planks; he gained the opposite side; and now Ichabod cast a look behind to see if his pursuer should vanish, according to rule, in a flash of fire and brimstone. Just then he saw the goblin rising in his stirrups, and in the very act of hurling his head at him. Ichabod endeavored to dodge the horrible missile, but too late. It encountered his cranium with a tremendous crash,—he was tumbled headlong into the dust, and Gunpowder, the black steed, and the goblin rider, passed by like a whirlwind.

The Legend Of Sleepy Hollow by Washington Irving

Of all the ghost stories I’ve heard or told over the years, the legend of the headless rider and his frantic chase of the hapless school teacher have touched me since I first heard it as a child. I remember times of riding my own horse growing up where I would gallop across the pasture pretending to be Ichabod riding Gunpowder for my escape across the bridge or depending upon my mood, pretending to be the headless specter chasing him down. I’m sure I am not the only one because The Legend Of Sleepy Hollow is known to be one of the oldest American ghost stories.

The town exists to this day and my first stop of the visit would be the old church bridge (now referred to as The Headless Horseman Bridge) which Ichabod thundered across in his attempted escape. While the original wooden bridge was replaced in 1912 you can still walk across the same path as the story. I might even have Kelly chase me across it and then throw a pumpkin at me. [NOTE FROM KELLY: I would SO do that]

Vintage postcard showing the Headless Horseman Bridge in Tarrytown, N.Y. (Wikimedia Commons)

My next stop would be the Sleepy Hollow Cemetery. As luck would have it, there is a replica bridge over the Pocantico River that locals say is the original site of the bridge in the story. This bridge does more reflect the nighttime ride and it sits where the story marks at the bottom of a grassy knoll in sight of the mill pond and the Old Dutch Church which also remains to this day.  In the cemetery you can visit the grave of Washington Irving, the graves of the Van Tassel family and William Rockefeller who along with his brother J.D. founded Standard Oil Company. If that isn’t enough, there is a marker with a woman sitting in a chair who as legend says roams the cemetery at night.

The town also plays up its headless horseman connection and every Halloween in non-Covid times offers multitudes of events and hosts tens of thousands of people from around the world.

A car driving across the HEadless Horseman Bridge in Tarrytown, N.Y. Note the historical marker. (Wikimedia Commons)

“The bridge became more than ever an object of superstitious awe; and that may be the reason why the road has been altered of late years, so as to approach the church by the border of the millpond. The schoolhouse being deserted soon fell to decay, and was reported to be haunted by the ghost of the unfortunate pedagogue and the plowboy, loitering homeward of a still summer evening, has often fancied his voice at a distance, chanting a melancholy psalm tune among the tranquil solitudes of Sleepy Hollow.” 

~ The Legend Of Sleepy Hollow by Washington Irving

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