Exploring Westchester: Historical Charms and Mysterious Legends

Exploring Westchester: Historical Charms and Mysterious Legends
Credit: Unsplash

Nestled just outside the bustling New York City, Westchester County offers more than meets the eye. While often associated with affluence and an upstate atmosphere, this 500-square-mile community of nearly one million residents holds a treasure trove of captivating history and urban legends. Join us as we explore some of the intriguing tales that make our county truly unique.

Sleepy Hollow

Exploring Westchester: Historical Charms and Mysterious Legends
Credit: Chris Boese

The Legend of Washington Irving In the Dutch settlement of Tarry Town, immortalized by Washington Irving, lies the legendary tale of the Headless Horseman. In 1996, Tarrytown officially embraced this lore by adopting the name “Sleepy Hollow.” Visitors can experience the ghostly haunts of the famous literary character and pay homage to Washington Irving at his final resting place.

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Exploring Westchester: Historical Charms and Mysterious Legends
Credit: Minard38

The town of Harrison owes its name to John Harrison, surrounded by intriguing legends. According to the local historian, one popular tale recounts an Indian chief named Pathungo selling Harrison as much land as he could cover on horseback within 24 hours. This resulted in the unique circumstance of Harrison being a landlocked community close to Long Island Sound.

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Exploring Westchester: Historical Charms and Mysterious Legends
Credit: Ed from Queens, USA

The Espionage of Major John Andre In Tarrytown, Army Major John Andre, a British soldier, met his demise at the hands of three militiamen. Disguised in civilian attire and armed with a pass from Benedict Arnold to cross American lines, Andre’s true identity was revealed during a search. His capture exposed Arnold’s treasonous activities, uncovering detailed plans of West Point’s fortifications. Andre was convicted as a spy and ultimately sentenced to hanging.

Buckout Road

A Haunting Legend West Harrison is home to the eerie stretch of road known as Buckout Road, shrouded in a chilling legend. According to the tale, if you stop at the red house and honk your horn three times, cannibal albinos emerge to claim unsuspecting victims. This macabre story has gained such notoriety that a former New Rochelle resident seeks to bring it to the big screen.

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Son of Sam

Unveiling the Son of Sam’s Yonkers Connection Infamous serial killer David Berkowitz, known as Son of Sam, left a dark mark on New York City in the 1970s. However, it was in Yonkers, where Berkowitz resided, that he was ultimately apprehended. The parking ticket he received earlier that day, along with a witness account of him in the getaway car, led to his arrest. Berkowitz was sentenced to 365 years in prison.


The past events of our community shape its identity and bring us together. Westchester County’s rich history and legends far surpass any preconceived notions of affluence or upstate location. Join us in embracing the captivating tales that belong to our remarkable county.

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