Eat, Drink, and Be Scary!

Halloween’s Westchester history

This year, American farmers will likely plant approximately 50,000 acres of pumpkins. More than 7,000 of the orange squash will be hand-carved into illuminated jack o’ lanterns to the fright and delight of those in attendance at the Great Jack O’Lantern Blaze, held annually at the 18th-century Van Cordlandt Manor in Croton-on-Hudson.

With the Headless Horseman of Sleepy Hollow and a plethora of national historic sites-turned-haunted houses, Westchester is an epicenter of Halloween in the US.

The spooky story dates back to a Celtic festival called Samhain, in ancient Ireland. The celebration marked the end of summer, when the cold set in and death crept across the countryside. In turn, it was thought that the invisible line between our world and the next evanesced. A twilight zone conjured apparitions of past phantoms and ominous visions of the future. 

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The prescription for protection: a celebration with animal skins and masks that would scare off errant spirits.    

When the Romans conquered Britannia around the turn of the millennium, they brought with them traditions around Samhain that honored both the dead and the fruit harvest (a possible explanation of the bobbing-for-apples tradition). 

As the customs melded, Christianity’s spread led to All Saints’ Day—aka All Hallows’ Day, celebrated on November 1—in an effort by the pope to turn pagan holidays toward piety. The holy dressed as popular saints on All Hallows’ Eve, which was soon shortened to “Hallowe’en.”

By the 19th century, Ireland’s potato famine had driven Irish immigrants to the States, and with them came Halloween. Washington Irving’s famed The Legend of Sleepy Hollow emerged as an inspiration for New World Halloween lore. While many Northern European legends mention a headless horseman haunting the countryside, the 1820 Washington Irving classic brought to Westchester a tale that has remained in continuous print ever since. The story’s fall backdrop and Hudson Valley setting intertwined with the rituals of Samhain. Some artists have reimagined Irving’s horseman carrying a pumpkin instead of a head, linking the tale with Halloween. 

While Puritan temperance limited celebrations in 19th-century America, traditions that had evolved, such as etching dead faces into gourds, remained popular. Before long, Halloween found a home in modernizing suburbia, including Westchester. Villages planned town-wide events, where families exchanged treats and games. Keeping with Halloween’s harvest heritage, pumpkins and apples were more common than candy. For many, toys and money landed in the goody bag more frequently than food.

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As Halloween trick-or-treating spread across America’s cities and surrounding neighborhoods—perhaps to appease young teens looking for mischief—confectioners saw an opportunity to sweeten their bottom lines. Wrapped candy attracted parents worried about the safety of homemade food doled out to their kids from the hands of strangers.

In 2015, the average American spent nearly $75 on Halloween goods, from sweet treats to face paint, with total spending exceeding $6.9 billion. 

This year, Westchesterites can pay a Halloween visit to the Sleepy Hollow cemetery to see Washington Irving’s tombstone alongside those of Andrew Carnegie, Elizabeth Arden, and William Rockefeller. And if the Celts were right, and the pall between the living and dead does recede, perhaps you’ll talk to them, too.  


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