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White Plains, Westchester, NY, United States for Westchester Halloween Traditions – Seasonal Fun in the Home of the Headless Horseman

Can you feel it? The anticipation is building, now that October has arrived, for Halloween and all the spooks, treats, and excitement that comes with it. We dare you to step outside of your normal Halloween routine, and escape for a weekend to the home of the Headless Horseman.


Westchester County, New York transforms into a Halloween haven every single fall season. Is it because of Sleepy Hollow, home of the Headless Horseman, is within Westchester County? Perhaps… Or is it because Westchester is simply spooky? You’ll need to visit to find out, and if you do, you won’t want to miss these festive adventures… If you dare.

Sleepy Hollow Headless Horseman – If You Dare!

Scare Factor – Extreme – at Horseman’s Hollow

sleepy hollow headless horseman
Source: Visit Sleepy Hollow | Facebook

Sleepy Hollow is a real town, in the very real Westchester County, New York. Yes, the very town that the headless horseman is said to have been just before becoming headless. Doomed to forever exist in a sort-of-dead headless state, the Horseman has since taken (since 1776) to haunting one season out of the year – Halloween. For the eighth year in a row, Horseman’s Hollow returns at Philipsburg Manor, transforming the already spooky tale into a modern-day nightmare. This event is scary for real, and should only be visited by those prepared to be scared!

The Greatest Jack o’Lantern Display of All Time

No question about it, The Great Jack o’Lantern Blaze is the most epic Halloween display ever. There’s nothing quite like it, and if you only have time to do one activity, this is it! Wander through a historic, 18th-century riverside landscape while taking in the breathtaking display of over 7,000 illuminated jack o’lanterns. Every single jack o’lantern is individually designed and hand carved by a team of artisans.

Plan Your Spooky Escape

Hear The Legend of Sleepy Hollow From a Master Storyteller

Washington Irving was a genius writer, exhibited best by his tale The Legend of Sleepy Hollow. Jonathan Kruk is a master storyteller, and verbally and visually brings Irving’s tale to life for audiences in the Old Dutch Church, across the street from the Philipsburg Manor.

A Murder Mystery in The House of Curiosities

Each Halloween season the Lyndhurst Mansion comes alive with spookiness and Halloween decor for the annual Jay Ghoul’s House of Curiosities production. This year a murder has taken place, and the Gothic mansion is filled with suspects, each holding a clue to the crime. During the 30 minute production, you’ll move through the first floor and the basement, meeting various characters as you go. It’s up t you to solve the case or else the madman will escape!

Experience the Sleepy Hollow Cemetery

Though the name Sleepy Hollow reminds most of the infamous tale, it’s been a very real place for centuries, and its cemetery is the resting place for notable individuals such as Andrew Carnegie, Brooke Astor, and William Rockefeller. Throughout October, the cemetery has an array of fascinating events including An Evening With Edgar Allan PoeSpooky Stories From Six Feet Under, Dark Dahl, and Beyond the Legend: Irving’s Ghost Stories. Learn more about the various ways to explore the cemetery here.

You May Also Enjoy: Breathe in The Fresh Winter Air of Rye Brook, New York For The Perfect Family Getaway

Whether you want to be scared out of your mind, entertained with Halloween tales, or fully immersed in the mystique of Halloween, Westchester County has something for everyone. All Halloween styles are represented here, and one doesn’t have to search hard to find spooky fun. Treat yourself to a weekend escape; book cozy and central accommodations at Doral Arrowwood Resort.

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