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Visit the real Sleepy Hollow, and the places the Headless Horseman haunts in Washington Irving’s tale
Halloween is here, and there’s no better place to spend a spooky afternoon than the Westchester County villages of Tarrytown and Sleepy Hollow in New York state, an easy Metro-North Railroad or car drive from New York City.
This is the hilly countryside where author Washington Irving lived, and where he set his 1820 tale “The Legend of Sleepy Hollow.” It was here that Irving unleashed the Headless Horseman — a decapitated Hessian soldier who rises from the Old Dutch Church’s graveyard in quest of his head — on the hapless schoolmaster Ichabod Crane.
Spend an afternoon tracing Irving’s haunts, and those of his legendary characters. Find it all on an easy and short walk along Broadway.
Stop 1: Christ Church
At Broadway and West Elizabeth Street in Tarrytown, admire the Christ Episcopal Church, where Irving worshipped.
By one account, the facade’s ivy is said to descend from a cutting taken at Irving’s beloved Sunnyside (914-631-8200), a picturesque villa on the Hudson, which you can also visit and I strongly urge you to do so.
Stop 2: Main Street
Walk north a block to Main Street. You can take in the 19th century ambiance while antiquing. Nourishment nooks include Lefteris Gyro and Coffee Labs, all inside the Tudor-style Washington Building, the former site of an inn visited by George Washington.
Next door, The Music Hall is an 1885 Queen Anne brick masterpiece.
For a drink, tarry at the Set Back Inn (914-631-9740) — after all, Irving jokingly suggests in "The Legend” that the town got its name because of the local farmers who tarried on market days.
Stop 3: Landmark Condominiums
Get back on Broadway and walk north a block to the intersection with Hamilton Place, where you’ll find the Landmark Condominiums, graced with a large, lush lawn out front.
This land was once part of the Van Tassel farm, and a long-gone Van Tassel building where the condos now stand may well have been Irving’s inspiration for “The Legend” character Katrina Van Tassel’s home. (More here on the question of where it actually was. Let’s just go along with the idea it was exactly here for our purposes today.) The party there drew lanky Ichabod and big-bully Brom Bones, who vied for the “plump as a partridge” catch.
It is from here that we can visualize awkward Ichabod setting off down Broadway on his unreliable steed, Gunpowder.
Stop 4: Andre monument
Farther north on Broadway, about a half block past the 1929 Warner Library at the intersection with Wildey Street, is the Andre monument in Patriots Park. It’s a tribute to three patriots who captured Major John Andre, a British spy.
The encounter actually happened about 200 yards east, but the spot is not marked because this part of the road was rerouted. In “The Legend,” the Andre intersection is significant, as it’s where the horseman encounters Ichabod and gives chase. The brook Irving mentions still runs through the pretty park.
Stop 5: Broadway and Beekman
Past the brook, you’ll enter Sleepy Hollow proper. Continue on Broadway to the intersection with Beekman Avenue, the main shopping drag of Sleepy Hollow.
It is home to the Sleepy Hollow Municipal Building and tarry-worthy watering holes such as J.P. Doyle’s (914-631-3015) and, up on Broadway, the new Horseman Bagels shop, which replaced the beloved Horseman Diner but at least kept the horseman “brand.”
Stop 6: Old Dutch Church and Sleepy Hollow Cemetery
Finish your jaunt down the hill along Broadway toward the Old Dutch Church.
Before you get there, be sure to admire to two Headless Horseman sculptures.
The one, below, sits besides the parking lot at the Historic Hudson Valley visitor center (914-631-8200), which is a requisite stop to plan your day visiting sites like Kykuit (the Rockefeller estate) and other notable locations.
Just across Broadway, on a traffic island across from a service station, is a depiction of the Horseman chase rendered in layers of corten steel.
The late 17th century gambrel-roof church is on your right past the Headless Horseman Bridge, a successor to the original span that was farther east inside the cemetery (a pipe bridging the Pocantico River roughly marks the spot.)
It’s at the original bridge site where the horseman finally polishes off poor Ichabod. (Irving hints that Brom, who won Katrina, disguised himself as the horseman to scare off the superstitious Crane, but townies in the tale believed the specter whisked Ichabod away.)
The Dutch burial ground has evocative gravestones, and the deceased include some real-life inspirations for Irving’s tales, such as Katrina and Brom. The adjacent Sleepy Hollow Cemetery is home to many famous dead, including Brooke Astor and Leona Helmsley.
Guidebooks are at the visitor’s center I mentioned across the street at Philipsburg Manor, the restored mill where Ichabod flirted with the Hollow’s lovely ladies. This time of year, you will also see it and other Horseman souvenirs for sale at the cemetery’s main gate.
As for Irving, he rests on a hill in Sleepy Hollow Cemetery, looking below on the land he immortalized.
What’s in a name? Sleepy Hollow was called North Tarrytown between 1874 and 1997. Voters approved the name change in part to celebrate the village’s Headless Horseman heritage and help rebound from the loss of the General Motors plant at the base of Beekman Avenue.
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