"From the listless repose of the place, and the peculiar character of its inhabitants, who are descendants from the original Dutch settlers, this sequestered glen has long been known by name of Sleepy Hollow ... A drowsy, dreamy influence seems to hang over the land, and to pervade the very atmosphere."
Nothing sets the tone for Halloween quite like a good ghost story, Washington Irving's "The Legend of Sleepy Hollow" is a classic-- in fact, it might even be one of America's original classics, one that people still reference today. Set in the Dutch settlement of Sleepy Hollow, just outside Tarrytown, New York, it tells the tale of how outsider Ichabod Crane vied with local Abraham "Brom Bones" Van Brunt for the heart of Katrina Van Tassel, the daughter of a wealthy farmer. Woven throughout the short story are references to the many spooks and spectres who also inhabit Sleepy Hollow. After Crane's plan to propose to Katrina falls through, he's scared out of town by one of the hamlet's most infamous ghosts-- the Headless Horseman, the spirit of a Hessian soldier who had his head blown off by a cannonball during the American Revolution. Or, at least he's frightened by what he thought was the Headless Horseman...it's implied that it was Brom Bones all along, holding a pumpkin meant to look like the Horseman's severed head.
In 1997, North Tarrytown renamed their little village "Sleepy Hollow" so you can visit and look for the Headless Horseman yourself-- although it probably won't be too difficult, since the local high school's mascot is the Horseman. Or, you could visit Sleepy Hollow and check out the local fall fun!
First stop by Irvington, New York, where Washington Irving himself once lived. See the scenic and totally peaceful grounds where he drew inspiration for characters like Rip Van Winkle and Ichabod Crane, and get a feel for the time and place where he set his stories. You'll be led through the estate by a costumed interpreter who can provide all kinds of insight into the life and times of Irving.
Then stop by the town's historic Lyndhurst mansion, which, in addition to being a totally strange-looking Gothic mansion served as a filming location for movie adaptations of the horror-themed soap opera "Dark Shadows". The winding drive to the quirkily designed mansion and the 19th century conservatory make this absolutely worth a visit. And, around Halloween, it transforms into Jay Ghoul's House of Curiosities, a spooky haunted house
You can also see the Headless Horseman Bridge... or, at least, a really old bridge that serves as a kind of replacement for what could have been the bridge where Ichabod Crane has his famous encounter with the Headless Horseman. The bridge from back when Irving was alive has since rotted away, but this 1912 replacement has the quaint, old vibes that make it perfectly quiet... and perfectly ripe for a Hessian ghost haunting.
Van Cortlandt Manor is a great place to stop by and experience the rich Dutch history that played a role in the story. Learn about the prominent Van Cortlandt family and see what life was like back in 18th century America, right as the country won its independence.
For Halloween, they have an annual Jack-o-Latern festival that features over 5,000 carved pumpkins (Headless Horseman sightings not guaranteed) which occurs on weekends between October 4th and November 9th.
And for good measure, here's Irving's epic description of the town's lovely fall foliage:
"It was, as I have said, a fine autumnal day; the sky was clear and serene, and nature wore that rich and golden livery which we always associate with the idea of abundance. The forests had put on their sober brown and yellow, while some trees of the tenderer kind had been nipped by the frosts into brilliant dyes of orange, purple, and scarlet."
And also ghosts.