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Around the World: Halloween in Sleepy Hollow is Spectacular!

Jennifer Merin on

Washington Irving’s beloved classic “The Legend of Sleepy Hollow” certainly sets the scene for Halloween scares. Referring to the famously headless horseman who haunts the hood, this quote: “Indeed, certain of the most authentic historians of those parts, who have been careful in collecting and collating the floating facts concerning this spectre, allege that the body of the trooper, having been buried in the church-yard, the ghost rides forth to the scene of battle in nightly quest of his head; and that the rushing speed with which he sometimes passes along the Hollow, like a midnight blast, is owing to his being belated, and in a hurry to get back to the church-yard before daybreak”

Sleepy Hollow is a village in the town of Mount Pleasant in Westchester County, New York, and is located on the east bank of the Hudson River, about 30 miles north of New York City.

Anyone who’s read Washington Irving’s enduringly haunting tale can imagine that Halloween floats into Sleepy Hollow with a rich array of ghostly tourist events, many of them based on or located at sites associated with the story of the Headless Horseman and the early 19th century author who penned his tale.

Using the story as a guide map, you can experience a wonderfully entertaining and spooky road tour.  Most of the legend’s locations are located within a radius of several miles, and some are in such close proximity that they’re within walking distance of each other.

For starters, you can easily trace Ichabod Crane's famous ride up the Albany Post Road (now named Route 9, Broadway). There are at present several suggested sites for the Van Tassel farm, but the most popular assumption is that Washington Irving was thinking of the former Elizabeth Van Tassel house, which was located at what is now the northeast corner of Hamilton Place and North Broadway in Tarrytown.  The XLandmark Condominium building now sits on the site.

If you continue walking (or driving) north from site of the Elizabeth Van Tassel house, for about  0.3 mile on Route 9 (North Broadway), you get to the Andre Captors' Monument in Patriots Park, the spot where Ichabod Crane was met by the Headless Horseman.

Actually, the marshy terrain described by Washington Irving has been drained, but there is still a stream that flows through Patriot Park. Andre Captors' Monument marks the historic place where patriots John Paulding, David Williams, and Isaac Van Wart captured British spy John Andrenand exposed Benedict Arnold's treasonous attempt to turn over West Point to the British. That was on September 23, 1780, years before Washington Irving wrote “The Legend of Sleepy Hollow,” but it is the same location where Ichabod encountered the sentry. The place isn’t all that spooky now--well, not in daylight anyway--but you can, if you want to exercise your imagination, make a mad dash, as did Ichabod, along Broadway until you reach the Old Dutch Church. It’s about 0.6 mile away.

The yard of the Old Dutch Church is where Ichabod sought refuge from the Headless Horsemen.  The adjacent Sleepy Hollow Cemetery had not yet been established at the time Washington Irving wrote his famous tale. But, the historic burying ground is the final resting place for actual historic figures who were probably role models for Washington Irving’s characters--Katrina Van Tassel, Brom Bones and others in the story--and is also believed to be the main haunting place of a headless Hessian soldier--or the Headless Horseman.  You can learn all about the graveyard’s real and ethereal inhabitants while taking interpretive guided tours or a self-guided tour using the fold out map that’s available at Philipsburg Manor, just across the road from the Old Dutch Church of Sleepy Hollow on Route 9.

Philipsburg Manor, a manor house and grist mill built by Frederick Philipse, who also constructed the Old Dutch Church of Sleepy Hollow, now serves as a living history museum with wonderful exhibits about Sleepy Hollow's agrarian past. The millpond beside the typical Dutch manor house is where Ichabod Crane often strolled.

Sleepy Hollow Cemetery, which actually surrounds the Old Dutch Burying Ground, is where you’ll find author Washington Irving’s grave, located in the southern end of the cemetery in a plot overlooking the old church and its burying ground. In addition to Irving, more modern celebrities buried in Sleepy Hollow Cemetery include Andrew Carnegie, Walter Chrysler, William Rockefeller, and Elizabeth Arden. You can locate their graves on a map of the grounds that’s distributed free of charge at the cemetery office, which is located about a quarter of a mile north of the Old Dutch Church on Route 9 (North Broadway).

The map will also point you to the Headless Horseman Bridge in Sleepy Hollow Cemetery. Nobody knows the exact location of the old timber bridge where Ichabod Crane was unseated by a pumpkin, but locals say it would probably have been located to the east of the current Route 9 Bridge (on Sleepy Hollow Avenue), which crosses Pocantico River inside Sleepy Hollow Cemetery about 0.3 mile inside the cemetery's south gate. Like the original bridge, the newer version is constructed of rough-hewn boards that creak and clatter when vehicles pass over them. Eerie, it is.

Nobody is suggesting that Washington Irving’s own home, located on West Sunnyside Lane, off Route 9 (South Broadway) in Tarrytown, is haunted, but it is beautifully restored and furnished with the author's writing desk, books and other possessions. The property was built as a Dutch farmer’s house, but it is now owned and maintained by Historic Hudson Valley, a nonprofit historic association, which offers tours to the public.

Travelers’ fascination with “The Legend of Sleepy Hollow” hasn’t been overlooked by local tourist operators, either.  The popular Headless Horseman Hayrides attraction in the Hudson River Valley’s Ulster Park is in full gallop around Halloween.  This family-oriented entertainment includes a one-mile hayride, corn maze and three haunted houses--and several gift shops, of course.  It’s very touristy, and a lot of fun. You can learn more about it at

You can learn more about Hudson River Valley tourism--both Halloween-related and general--at


Copyright 2019 Jennifer Merin


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