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Real Places from the Legend of Sleepy Hollow

by on October 16, 2013

Ichabod Crane–schoolmaster, ladies’ man and nervous wreck–takes us through the picturesque Dutch community of Tarrytown, New York in Washington Irving’s classic story The Legend of Sleepy Hollow. The remarkable thing about this area, is that it’s easy to imagine Ichabod being chased by the Headless Horseman to this day. Not that there aren’t paved roads or jet planes passing by, but many of the locations that writer Washington Irving drew inspiration from are much like they were during his lifetime.

philipsburgPhoto credit: Wikipedia

It doesn’t get any more Dutch than Philipsburg Manor, which has been restored to the 17th century manor that Irving wrote about. This is where schoolmaster Ichabod Crane, something of a ladies’ man, strolls with local girls.

bridgePhoto credit: Visit Sleepy Hollow

Carriage roads still meander along the Pocantico River, which is the same route Ichabod Crane takes when he travels to and from the Van Tassel homestead party, late one spooky night.

Landmark_CondoPhoto credit: Sleepy Halloween

Did you know that the Van Tassels were actual people who Irving fashioned his characters after? This is the location of the Van Tassel homestead, where Ichabod becomes bewitched by the town’s coquette, Katrina Van Tassel. The building was turned into a tavern during Irving’s day. Look for a bronze marker on the southwest corner of the Landmark property, noting that this is the site of the Mott Tavern.

rockPhoto Credit: Lucas Buresch

While at the Van Tassel party, Ichabod listens to local ghost stories. One involves Raven Rock, the haunt of a woman in white. Her screams could be heard by passersby. Ichabod, easily freaked out, is primed for a nervous ride home, which would take him near this very site.

churchPhoto credit: Carlos G.

The Old Dutch Church and Burying Ground is where the tale of the Headless Horseman begins and ends. It is the burial site of the horseman, who allegedly lost his head in battle, and emerges from the grave each night in search of it. The writer of this spooky tale, Washington Irving, is buried here himself!

Capture_of_John_andrePhoto credit: Wikimedia Commons

Patriot’s Park. The site where an American soldier, acting as a spy for the British during the Revolutionary War, was caught. John André was executed for his crime–conspiring to hand George Washington over to the British–and America was saved from considerable disaster. It’s also where Ichabod Crane encounters the Headless Horseman for the first time.

sunnysidePhoto credit: Montgomery Place

Not a location in Irving’s story, but a place dear to his heart–his house. Sunnyside, Irving’s “cottage” on the Hudson River, is a museum open to the public. The buildings have been restored to what they were in Irving’s day. He even died here, in his bedroom, on November 28, 1859.

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