Visit Where The Legend of Sleepy Hollow Began

Legend tells the story of Ichabod Crane, a scrawny school teacher from Sleepy Hollow who takes a fateful ride into the forest and confronts the ghost of the Headless Horsemen. This story, penned by Washington Irving in “The Legend of Sleepy Hollow,” insinuates that the Headless Horseman was not really a crazed ghost or killer, but rather a fellow townsman looking to prey upon Ichabod’s superstitious nature. In his movie, Tim Burton makes Sleepy Hollow the setting for a string of murders, and Ichabod the beautiful Johnny Depp, a slight (but welcomed) character change from the original story. The misty haze and brushwood in the film, however, is not far from the truth of the surrounding woods of Sleepy Hollow Village, on a cold, autumn day.

Sleepy Hollow

Sleepy Hollow Village is more than a legend, in fact it is a small part of Tarrytown NY, just 40 minutes north of New York City. The village itself is pretty customary of the surrounding area. The boutique shops, colonial architecture, and overall greenery contribute to the small town air. The village officially changed its name to Sleepy Hollow in 1996, in order to commemorate Washington Irving’s story, and no doubt take advantage of the tourist draw, especially this time of year before Halloween.

The town recreates the legend at Philipsburg Manor, where people dressed up as ghosts and ghouls will great you as you tour the grounds. There is even a Headless Horseman riding around with his pumpkin head. The reenactment is fun, but it is not exactly the place for thrill seekers looking to be scared this Halloween, although getting lost in the surrounding small towns and dark forests was not a pleasant experience. For someone like me, who loves fall and all of its components (apple cider, pumpkin spice, apple picking) it is a fun trip. Nearby there is a pumpkin art installation (yes you read correctly) called the Great Jack O’Lantern Blaze. It is much more secluded and creepy than the reenactment at Sleepy Hollow. There are what seems like thousands of carved pumpkins and figures spread out another manor. The Historic Hudson Valley has all the details you need for your visit.

The infamous Headless Horseman.