Legends and Lore of Sleepy Hollow and the Hudson Valley


Get the to the source of Washington Irving’s classic!  I’ve gathered the backstories of the ghosts and characters abounding in “The Legend” in this blend of story and scholarship. Discover the curse of Sleepy Hollow.  Uncover the spirits ofMother Hulda, the Wailing Women in White and Unfortunate John Andre.

Here to is the origin story of the iconic Headless Horseman of Sleepy Hollow, featured on The Travel Channel.

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 Philipsburg Manor and near by 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 confidante 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 The Lore of The Headless Horseman of Sleepy Hollow.

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, 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 stories American launched the legend.  A clever mix of characters from the new nation, a little romance, culminating with ghostly chase, turned this tale into a tradition for telling and retelling.

“The Legend” inspired books, plays, ballets, a half a 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 the Jesse Merwin. A New England school  teacher 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 descendants 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 Tarryteon 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 of America 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 reeking 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 haunter. 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 “story-teller” 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 long 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 re-enactor 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.”


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