All About Halloween in Sleepy Hollow

Blazing orange lanterns, eerie vibes, old manors, and a famous spooky tale of a headless horseman – that’s what Sleepy Hollow is all about. Made famous by Washington Irving’s novel with the same name of the place, Sleepy Hollow attractions makes it the best place to visit for Halloween not only because of their Halloween activities but also because of the legends and the old structures in the horror novel that still stands today.

Sleepy Hollow’s “Welcome” sign into the town
Photo credit: Youtube screen grab

While this old town is a great visit any time of the year, here are the things to do in Sleepy Hallow during Halloween that are sure to send a chill down your spine, especially in the times when ghouls and ghosts run free.

If you want to go back in time to a more medieval setting, celebrate Halloween in Romania – all the way to Transylvania where Dracula awaits you in his castle.

Philipsburg Manor

Philipsburg Manor as it stands presently
Photocredit: Wikimedia Comms

Overlooking the Pocantico River, this 18th-century manor was a bustling gristmill during the 1700s. The property that was once occupied by European farmers under the Philipse name holds a dark history. The Manor was home to 23 African slaves that spend their dreadful days working at the mill. Today, the Manor acts as a museum to bring awareness to the history of the African slaves and their struggles during the time.

Visitors are greeted by staff dressed in the 1750’s attire who tells you the stories and history of the manor, taking you back to the 18th century as you explore the Philipsburg Manor Houses’ interior and wander along its wooden path.

The Famous Cemetery

Entrance to the Sleepy Hollow cemetery
Photo credit: Shutterstock

There is no better way to get into the feel of the supernatural festival than an old-school Halloween cemetery tour. That said, the Sleepy Hollow cemetery is much more than a location for a spooky event.

This is where you’ll find Washington Irving’s grave, the famous writer who put Sleepy Hollow on the maps through his hair-raising novel. Other historical figures like William Rockefeller, Walter Chrysler, and Andrew Carnegie also rests here. Because of these notable figures, the cemetery is listed on the New York State and the National Registers of Historic Places.

The cemetery opened in 1849 and stretches to 85 acres. The Pocantico River runs through the cemetery, making it a beautiful place for the good souls who rests there.

During the Halloween events, this old town holds a special Sleepy Hollow lantern tour, where the visitors and travelers are taken around the graveyard with carved Jack-o-lanterns lighting up your path in the eerie darkness.

A lantern lit and glowing on a tombstone
Photo credit: Ivan Radic via Flickr

For a darker experience, the Sleepy Hollow cemetery tour also hosts the Murder & Mayhem event where visitors will be taken to the graves of some of the most vicious residents that dabbled in murder and chaos while they still breathed. While these stories are horrifying they are all very true. And who knows, they may still be breathing.

The Old Dutch Church

Side view of the Old Dutch Church
Photo credit: James Russiello via Wikimedia

This oldest church in New York is world-famous for its appearance in “The Legend of Sleepy Hollow” novel. It’s where Ichabod courted Katrina and where the Headless Horseman spent his days haunting the area.

The church was found in 1685 and was already old enough when Irving set his eyes upon it before penning his novel. It sits at the same site as the Sleepy Hollow cemetery and is open to visitors who want to walk around the spooky site that bought the legendary horror story into existence.

Headless Horseman Bridge

A redesigned version of the Headless Horseman Bridge

Surrounded by the eeriness of dense trees and the rushing sound of the river below, the Headless Horseman Bridge is one of the most visited and popular site in Sleepy Hollow.

In Irving’s gothic novel, this is the spot where the main character, Ichabod, runs to after being chased by the Headless Horseman through the woods at night. Though the bridge standing now has been redesigned, it still captures the spooky essence of the place. It’s the perfect spot to click a Halloween inspired image and to take creepy walk in the forest when the sun goes down.

Digital image of the headless horseman character from Washington Irving’s The Legend of Sleepy Hallow.
Photo credit: istock

If you want to have the hair-raising experience of being chased by the Headless Horseman, climb aboard the hay wagon and roll your way down in this Sleepy Hollow Halloween event. The ride takes you through the exact path where Ichabod ran for his life from the Hessian ghost horseman.

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