Legends and Lore of Sleepy Hollow & the Hudson Valley

book by Jonathan Kruk

My editors at the History Press reminded me, while “collating and collecting,” that people want the facts found in these legends and folklore to tell a story. I write then not as a scholar or a historian but as your storyteller. I leap into this book, mindful of the sage advice given by the renowned Alabama storyteller Kathryn Tucker Windham. When asked which spooky tales we should tell, Kate declared, “The only ghost stories worth telling are ones that are true.”  I agree!

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The Preface

Who is the Headless Horseman of Sleepy Hollow? Why does he ride? Who are his kindred spirits and what are their stories? Where did Washington Irving find inspiration to write the Legend? What’s the local lore of the lower Hudson Valley?

Curiosity chases the legendary Headless Horseman of Sleepy Hollow today. Thousands gather every October at the sites most associated with this gallivanting ghost. They seek, at Philipseburg Manor and nearby at the Old Dutch Church, an authentic and uniquely American experience of Halloween.

Performing in Sleepy Hollow since 1996, as Historic Hudson Valley’s legend storyteller, people turn to me as an authority on the region’s lore. Then they make me their confidant on the subject of its local ghosts. They pepper me with questions, offer theories and share encounters regarding a legend almost two hundred years old. This keen continuous interest motivated the research and story gathering for Legends and Lore of Sleepy Hollow and the Hudson Valley.

The Headless Horseman first galloped into our nightmares as a chapter collected into The Sketch Book of Geoffrey Crayon, Gent. by Washington Irving in 1819. Legends and letters tell us that this wayward New York lawyer living in England grew nostalgic for his boyhood ramblings through the moody mists of the lower Hudson Valley. Inspired by various sources, some oral, some written, the brooding Irving penned The Legend of Sleepy Hollow. A desire at the time for American stories launched the legend. A clever mix of characters and a little romance, culminating with a ghostly chase, from the new nation turned this tale into a tradition for telling and retelling.

The Legend inspired books, plays, ballets, a half dozen major films, haunted hayrides and countless place names. Indeed, a myriad of sources moved Washington Irving to create his classic. Heartbreak over the death of his beloved Matilda Hoffman prompted The Legend’s plot. Further, it brought the lovelorn Irving to Jesse Merwin. A New England schoolteacher in the Hudson Valley, Merwin shared his personal experience of an old Dutch American custom. This revelation, along with a quick entry in a Revolutionary War officer’s journal, became the core of truth of The Legend. Detailed conversations with the descendents of New Netherlanders, including their servants and slaves, gave life to The Legend’s convincing characters.

Irving also enlivened his legend with elements found in German folklore. The biggest piece came from an old epic poem retold by Wilhelm Burger. Add a dash from Robert Burns, plus boundless imagination, and The Legend lives.

Washington Irving mentions and alludes to other ghosts of Sleepy Hollow. They haunt people too. When the crowd thins after a show, some tarry like the young Washington Irving did in Van Tassel’s Tarrytown tavern, once just down the Old Albany Post Road from Philipsburg. Curious, they call out for more about the valley’s spirits: “Who is this White Lady of Raven Rock?” “Have you heard of the witch, Mother Hulda?” “How do you stop Major Andre’s ghost?” “Why do skippers shorten their sails for Hudson River imps?” “Does the Headless Hessian gallop through Scarsdale?”

The Headless Horseman truly dominates those other spirits of the region. Let them escape from beneath big ghost’s cloak, and each one delivers a gripping tale. This book also gives the fateful story of Major John Andre’s ghost. I unearthed not just one but several White Ladies wailing warnings at Raven Rock. The origins of Sleepy Hollow’s curse in Native American lore are illuminated here too.

The Legend of Sleepy Hollow’s characters have provoked questions and claims as to who was the original. A former president of the United States even certified an acquaintance of his as a model for Irving. I address the genesis of Ichabod Crane, Katrina van Tassel, Brom Bones and Balt van Tassel.

The storied Hudson River provides a rich source of influence over Sleepy Hollow. People once feared river spirits called imps making mischief or wreaking havoc upon their sloops on the Hudson. Related tales of phantom ships, and revolutionary era ghosts, no doubt filled the head of the rambling Irving. The folklore given here of these spirits and some their history serves to complete this book. Finally, recent encounters with the supernatural are brought out to help illustrate Sleepy Hollow’s continued sway other the land.

People looking for answers on the lore of The Legend of Sleepy Hollow will find Washington Irving charmingly circumspect. He triply distanced himself from the sources of the Headless Horseman. The Legend’s stated author, “Geoffrey Crayon,” declares he found the story “among the papers of the late Diedrich Knickerbocker” (TLSH, 1).* This Dutch New Yorker goes on to proclaim he heard the tale from “a pleasant shabby, gentlemanly old fellow” (TLSH, postscript).

Further, when the gathering of Manhattan’s “most sagest and illustrious burghers” listened to that gentleman spin his yarn, they questioned the veracity of The Legend. The storyteller confessed: “Faith sir, I don’t believe the half of it myself!” People today, however, still persist in believing in the other half. They tend to agree with wise women of Sleepy Hollow, “the best judges of these matters” (TLSH, 74); supernatural spirits, they assert, abound in Sleepy Hollow!

The Legend offers more than Washington Irving’s imaginative twists and romantic turns. There’s a surfeit of stories here waiting to be told. Gathered into this book are the origins of the Headless Horseman, the stories of other Sleepy Hollow spirits, with the history and local folklore. My research uncovered facts most likely known but obscured by Washington Irving. The reenactor who often portrays the Headless Horseman at Historic Hudson Valley’s Legend event lead me to a West Point professor with proof of a Hessian decapitated at a battle Irving calls “nameless.” Reconstructing the events leading to this moment, I put forth at the heart of this book a plausible account for the galloping Hessian’s demise.

"A rollicking good time. Should be on the reading list of every visitor to the Hudson Valley."

"A must have for ghost and legend enthusiasts everywhere."

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