André's Tree: Even More Hidden History in The Legend of Sleepy Hollow

All the stories of ghosts and goblins that he had heard in the afternoon now came crowding upon his recollection. The night grew darker and darker; the stars seemed to sink deeper in the sky, and driving clouds occasionally hid them from his sight. He had never felt so lonely and dismal. He was, moreover, approaching the very place where many of the scenes of the ghost stories had been laid…

Washington Irving’s classic tale The Legend of Sleepy Hollow, which celebrates its 200th anniversary this year, is replete with symbolism and analogy—but it’s the short story’s hidden history of the American Revolution which makes it a perfect treat for anyone seeking out a little history, but also in the mood for a fright. André’s Tree delivers on both.

Major André’s tree, illustration for “The Legend of Sleepy Hollow”, pre- 1939, by Arthur Rackham (1867-1939), New York Public Library Digital Collection.

After an evening spent with the townsfolk recounting the many “fearful sights which he had seen in his nightly walks about Sleepy Hollow,” Ichabod Crane mounted “old Gunpowder,” and started for home. Thus began Ichabod’s fateful—and perhaps final—journey through the hills and streams of Sleepy Hollow, directly on a path towards the Headless Horseman. But before his encounter with the Horseman, Ichabod is struck by the ghostly energy surrounding not the headless Hessian, but a tree. The enormous, imposing, and ominous tree looming before him “was connected with the tragical story of the unfortunate André, who had been taken prisoner hard by; and was universally known by the name of Major André’s tree.”

For literary critics, John André and his tree symbolize loneliness, betrayal, and death while also lending a mysterious air to Sleepy Hollow’s landscape. Historically speaking, well, things are bit more complicated.

British intelligence officer Major John André was hanged as a spy on October 2, 1780. Though André did not meet his final fate in the village of Sleepy Hollow (unlike poor Ichabod), he was captured there, along the Sleepy Hollow/Tarrytown line to be more exact. Modern tourists can visit the site where three American militiamen arrested André and found incriminating papers stuffed into his boots. Not a tree but a large monument, dedicated by “the people of Westchester County” in 1853, marks the spot in Patriot’s Park off of U.S. Route 9.

Of the spot of André’s capture Irving paints quite a spine-chilling picture of an “enormous tulip-tree, which towered “like a giant above all the other trees of the neighborhood.” Its foreboding presence and tragic association had earned it “a mixture of respect and superstition, partly out of sympathy for the fate of its ill-starred namesake, and partly from the tales of strange sights, and doleful lamentations, told concerning it.”

The Capture of André 1780, New York: published by Currier & Ives, c.1845, Library of Congress

According to 19th-century sources, there really was a tree rumored to have an association with André, most notably cataloged by Irving’s friend and sometimes collaborator James Kirke Paulding in his 1828 New York travelogue, The New Mirror for Travellers. Paulding wrote of the local memory of a large tulip tree, “one hundred and eleven feet and a half high, the limbs projecting on either side more than eighty feet from the trunk, which was ten paces round.” According to Paulding, local tradition held that it was under this very tree where patriots first apprehended and searched Major John André before delivering him across the Hudson River to meet his fate (an interesting side note that is James Kirke Paulding’s cousin, John Paulding, was one of the celebrated militiamen who actually captured André). Could Irving have seen the tree and felt its spooky presence for himself? Probably not—Paulding tells us that at the turn of the century—20 years before Irving wrote Sleepy Hollow—the tree was struck by lightning and came crashing down. But with The Legend of Sleepy Hollow set in 1790, the fictional Ichabod Crane could very well have peered into the tree’s gnarled branches and pondered their secrets.

In the evening of storytelling that Ichabod attends at Van Tassel’s, he hears “many dismal tales…about funeral trains, and mourning cries and wailings heard and seen about the great tree where the unfortunate Major André was taken, and which stood in the neighborhood.” Set only 10 years after these historical events, the fictional characters in Sleepy Hollow would have remembered these dramatic local events well. After his capture near Sleepy Hollow, André was ferried over the Hudson River to Tappan, where at Washington’s headquarters at the DeWint House a military trial found him guilty of espionage and sentenced him to death by hanging. André was hanged in a field less than a mile from the DeWint House.

Perhaps Washington Irving imagined that his Sleepy Hollow residents were in attendance at André’s execution on October 2, 1780. Thousands of onlookers are said to have witnessed the event, which garnered sympathy from officers (General Lafayette is rumored to have cried) and civilians alike (including crowds of sobbing women). Moments before he pulled the noose around his own neck, Major André took a white handkerchief from his pocket and “after taking off his hat and stock, bandaged his own eyes with perfect firmness, which melted the hearts and moistened the cheeks, not only of his servant, but of the throng of spectators.” Eyewitness Dr. James Thacher saw the convicted spy meet his end, and witnessed his burial in a coffin “at the foot of the gallows, and the spot was consecrated by the tears of thousands.”

The drama of General John André’s real-life capture near Sleepy Hollow and subsequent hanging makes a fitting inclusion in Washington Irving’s short ghost story, which hinges upon Revolutionary War history just as much as its spooky elements. Not only is Ichabod Crane fearful of the ghost of a headless Hessian soldier, the town itself is “haunted” by the memory of an executed British spy, perpetuated by the looming presence of a “fearful tree.”

As Ichabod Crane proceeded past the tree towards the Horseman’s bridge, “suddenly, he heard a groan—his teeth chattered, and his knees smote against the saddle.” Was it really just “the rubbing of one huge bough upon another other,” or was it really the ghost of John André?

Happy Halloween!

Katherine Egner Gruber
Special Exhibition Curator, Jamestown-Yorktown Foundation


Read The Legend of Sleepy Hollow online.

Selected Sources

John André, Washington Library Digital Encyclopedia

John André, Westminster Abbey

A Spy for a Spy: John André Hanged, New England Historical Society

John Knight, “The Death and Resurrection of Major John André,” Journal of the American Revolution

Henry John Steiner, The Headless Horseman Blog