Spies, Spirits, and the Westchester Legends That Shaped America

Picture a crisp moonlit night along the Hudson River in Westchester County, NY. The year is 1780. Silence blankets densely wooded trails. The clatter of a lone horseman echoes through the forest, breaking the stillness. Is it soldier, a spy or the spirit of a restless ghost?

In Westchester, known as the Revolutionary War’s “Neutral Zone,” lawlessness fueled chaos and fear. Friendships were betrayed, loyalties turned, and lives were lost. While the war raged, spies traveled along county roads. The blood of soldiers stained the soil. Secrets and deceit inspired the creation of tall tales of ghouls haunting the county.

Spies and the supernatural are linked in Westchester’s Revolutionary War legends. Perhaps that sound you heard is a lone rider. Perhaps not. In Westchester, NY, in 1780, anything was possible.

The Betrayal That Almost Ended America

On a September night in 1780, British Major John André stepped ashore near Haverstraw in Rockland County. He planned to rendezvous with Benedict Arnold, a Major General in the American Army and Washington’s longtime friend. Arnold, likely motivated by financial gain, handed André plans for West Point—the “key to America,” according to Washington – that Arnold had weakened under the guise of preparing to rebuild. André’s boat was then driven off by Patriot fire. With no choice but to travel through Westchester to reach his allies, André tucked the secret papers into his boot. In Tarrytown, three militiamen discovered André’s “boot papers.” The militiamen turned André over to the Continental Army. The Army imprisoned André first in Armonk, and then in South Salem. Later, they brought him to Tappan in Rockland County where he was executed. Arnold narrowly escaped and defected to the British. Had Andre and the boot papers made it to the British in New York City, it is likely that West Point and the Hudson Valley would have come under British control, potentially forcing an American surrender.

Spies Who Helped Turn the Tides

General George Washington was not only a skilled patriot commander, but he also knew the value of secret intelligence to his war effort. Many know of the Culper Spy Ring based out of Long Island and led by Major Benjamin Tallmadge. But did you know that there were spy rings operating in Westchester as well? Two Westchester-based double agents, Elijah Hunter and Luther Kennicutt, repeatedly risked their lives to pass information back to the Americans. Networked to the highest-level British officers including Commanding General Sir Henry Clinton and Adjuvant General John André, Hunter’s secret intelligence helped the Americans avert a greater disaster when the British took control of Stony and Verplanck’s Point in May 1779. And Kennicutt was able to warn Tallmadge of Banastre Tarleton’s planned 1779 attack on Pound Ridge. Both Kennicutt and Hunter were lucky to avoid capture and certain execution when Benedict Arnold exposed their identities upon his defection to the British.

The Ghosts of War

Westchester holds an important place in American Revolutionary War history. Several events, people and locations have also inspired lore that continues to fascinate residents and visitors today. Two such tales have their origins in Sleepy Hollow. Washington Irving immortalized the first in his story, “The Legend of Sleepy Hollow.” Many trace his tale of the Headless Horseman—a Hessian soldier who supposedly lost his head to a cannonball—to the Battle of White Plains on October 28, 1776. The Hessians were fearsome, ruthless German soldiers who fought for the British. Many died in battles in Westchester. Some believe that the Hessian in Irving’s story still rides through the night—from the Old Dutch Church and Burying Ground to Battle Hill Park—in search of his head.

Another tale with Revolutionary War connections is the legend of Hulda, the witch of Sleepy Hollow. As the story goes, Hulda was a reclusive to be a reclusive herbalist who was shunned by her neighbors, despite leaving them medicinal herb baskets to counter starvation and sickness. When British troops advanced, Hulda took up her rifle. She killed several British soldiers before she was fatally shot. The villagers, recognizing their prejudice, buried Hulda in the Old Dutch Burying Ground. In 2019, headstone was installed to honor Hulda’s legend as an “Herbalist, Healer, Patriot.”

Buckout Road, which connects West Harrison and White Plains, is known as one of the most haunted roads in New York based on its Revolutionary roots. Locals believe that the Patriots executed British Redcoats on the road during the war. On certain moonlit nights, some claim to have seen the spectral figures of grim British Redcoats marching in formation. On Halloween, teens swarm to Buckout Road hoping to witness this and other spooky sights. Based on its ghoulish history, it’s not surprising that Buckout Road was the subject of a 2019 horror film.

Where Revolutionary History and Haunting Meet

Westchester County was the site of many profound Revolutionary War moments. County residents risked their lives as soldiers or spies to assure a future of life, liberty, and the pursuit of happiness for generations to follow. During that journey to freedom, many endured tragedy and treachery. This Halloween, visit Westchester to experience the legacy of Westchester’s Patriots and discover the soldiers, spies and restless spirits whose stories still echo through the county.