The Headless Horseman May Lead You,
But Sleepy Hollow Will Make You Stay

Adrea Gibbs

Sleepy Hollow. The name itself conjures immediate imagery to the minds of those who have been introduced in any way, shape, or particularly the form of the Headless Horseman, to the Legend of Sleepy Hollow by American writer Washington Irving. With incarnations of the original story dating back to, presumably, a 1908 black and white silent film version, depending on your generation, those mental pictures are left up to personal interpretation.  Perhaps your own memories invoke the Disney cartoon from 1958, Ichadbod!, the musical (yes, there was one, and an opera, as well), the Tim Burton entry featuring Johnny Depp, or maybe television’s derivations that have incorporated the likes of Scooby Doo, Shelley Duvall’s Tall Tales and Legends, or, the most recent entry, Sleepy Hollow, with Ichabod Crane as a former English professor turned turncoat turned time traveler to become a part of present time are central to mental ima-ginings. Regardless, there is an allure about the town, tucked into the Hudson Valley, that speaks as much to people today as it did to Irving, if only fictionally.

The honest-to-goodness history of the town called Sleepy Hollow, if only dealing in semantics, is relatively short, having only changed its name officially in 1997. When asked why the town had voted to make that change, Rob Schweitzer, Vice President of Communications and Commerce at Historic Hudson Valley shared, “The voters, of what was then North Tarrytown, wanted to get out of the shadow of the larger municipality of Tarrytown and celebrate and embrace the iconic history that Washington Irving gave to the area. The Village was tran-sitioning away from being a General Motors ‘factory town’ and saw heritage tourism as a future path.” Good plan, as the town formerly known as North Tarrytown, is steeped in both history and folklore. While, from what could be gathered, it is appears a preponderance of the tourists are enticed specifically because of the Headless Horseman, though many only know about the haunting figure and are lost for the details of the proper tale.

  Monument presented by the Centennial Committee to North Tarrytown in 1974 (Photo: Adrea Gibbs)

Monument presented by the Centennial Committee to North Tarrytown in 1974 (Photo: Adrea Gibbs)

Most that set their sights to visit will head straight for the heart of the story, the Old Dutch Burying Grounds and Sleepy Hollow Cemetery, if only as a starting point. Tucked within a three-acre area around the exterior of the Old Dutch Church, are interred the remains of some of the models for Irving’s well-known characters. Deb McCue, of the Old Dutch Church, is, literally, surrounded by the ghosts of those whose lives, if only in name, influenced varying aspects of Irving’s story. Employed within the hallowed walls of the church, she is a living contem-porary of those whose memories she helps to keep alive, so to speak, given her work, proximity, and personal interest in all things Sleepy Hollow. Outside, you’ll find Eleanor Van Tassel Brush, the archetype Katrina, with her aunt, Catherina, contributing the name, resting peacefully. When asked specifically about another slated to be at rest, McCue shared, “Supposedly, if you walk north from the tip of the eastern wall of the church for 50 paces you’ll stumble on the grave of the Headless Horseman.” 

The fact there were real people who appeared to have, in some part, inspired Irving’s colorful characters actually buried in the town intrigues. As to the foundation of the actual story, some will argue that Irving’s insight for the story came from local legends. One version says the town buried a Hessian solider, sans head, and each night he would search for that what was taken from his shoulders. Others say the story revolves around Eleanor and a family tragedy. During the Revolutionary War, her farm was overrun with soldiers and set on fire. She was desperate to locate her baby who was nowhere to be found. Conflicting narratives say a Hessian soldier either a) ran back into the burning house to look for, find, and save the baby, b) had taken the baby and hidden him in the barn for safekeeping, or c) found him hidden in the barn. Long story short, a Hessian returned Eleanor’s baby and for that, the family was eternally grateful. Later, when a headless Hessian soldier was found, the Van Tassel’s, out of gratitude what had been done for them, respectfully buried the unknown, headless soldier at the church. It may, or may not have been, the same solider, but you get the idea. There is most likely some truth behind the legend, at least in some teeny, tiny part.

Tourists from all over the world are attracted to Sleepy Hollow because of the Legend, many wishing to pay homage to the author. Interestingly enough, Irving is not buried among his inspirations in the Old Dutch Burying Grounds, but lies for eternity in Sleepy Hollow Cemetery which surrounds the former, but is a separate entity. Amidst his family members, overlooking the Church yard below, he can be found easily enough at the end of a series of small signs pointing the way to his grave marker for those who make the trek. Unless, of course, you are like me and simply wander aimlessly in the hopes of stumbling across his place of rest. Or the guy who asked me if I knew where Irving was, as he doing the same thing I just had. But, Irving is not the sole celebrity buried within that hallowed earth. Tucked between beautiful and touching monuments for both the Revolutionary and Civil Wars, stunning artistry in the form of statuary and headstone, are lots of interesting individuals and families. Industry and innovation giants Samuel Gompers, Andrew Carnegie, Walter Chrysler, and William Rockefeller slumber there. So, too, does notoriously nasty Leona Helmsly. The mere thought of her may scare away some folks from walking the grounds. 

If you weren’t aware when you drove into town that it had any association with The Legend of Sleepy Hollow, by the time you left, at the very least, you might be wondering what the not-so-lightly veiled references were all about. Street signs are bright orange with black lettering, featuring the Horseman. Shops are filled with charming and creative tchotchkes imprinted with the town spectre. Even the mascot for the high school is, you guessed it, the Headless Horseman. Frankly, the town is right to embrace it. Whether it was an actively promoted initiative or not, people would still come. Best to take both advantage and pride in the town’s history. McCue said, “You can’t get away from the Legend in Sleepy Hollow. People come to the Old Dutch because of the Legend, but after sitting in our church and feeling the presence of 331 years of worship in that sanctuary, they leave with something much greater. The businesses support the Legend and the Legend supports the prosperity of the village, I suppose. It’s a small town.”

Perhaps more intriguing? Sleepy Hollow is rife with wonderful stories about the American Revolution, witches, pirates, and abolitionists. If there ever was a town that was built for Halloween, like its Massachusetts counterpart, Salem, Sleepy Hollow fits the ticket. Hulda the witch, who was said to be both a holistic healer and doctor, is surrounded by her own mythology including her mass killing British soldiers. Captain Kidd, both before and after his becoming a pirate, haunted the area and stories continue to date that treasure he buried still lays in wait for some modern-day Indian Jones-type to discover. Amanda Foster, a freed slave from Arkansas, provided both assistance and refuge to fugitive slaves, later becoming the Mother of the Foster Memorial AME Church in Tarrytown. There is a rich, unique history tied to this little community that resonate with many who never knew about the varied sagas until they rode in courtesy of Irving’s imagination. This is no one-Headless Horseman village, as the layers of the proverbial onion continue to peel away, anyone visiting will come to understand.

In reaching out to the The Historical Society serving Sleepy Hollow and Tarrytown, a well-informed trio was able to provide some fascinating information. Sara Mascia, Executive Director for the organization, Henry Steiner, Sleepy Hollow Village Historian, and Tara Van Tassell, Historical Society Trustee, when asked if the portrayal of the community in various media sparks tourism, they collectively cited several examples. Included among these, the many books, plays, and films about the American Revolution and Capture of Major Andre, of which AMC’s Turn, stands as a current example that draws visitors. Disney’s Sleepy Hollow brings those who have a penchant for the nostalgic evoked in that version, although Tim Burton’s film seemed to create a limited buzz according to their sources. House of Dark Shadows enthusiasts still make their way to Lyndhurst (former home of railroad magnate Jay Gould and located in Tarrytown on grounds beside the Hudson River) and Sleepy Hollow Cemetery, where filming occurred for that novel soap opera treatment. And the present FOX series, Sleepy Hollow, has shown some impact, with an uptick in visitation for both Sleepy Hollow and Tarrytown coinciding with some area events that had started just prior to the show’s premier.

  Delavan Lot, Sleepy Hollow Cemetery (Photo: Adrea Gibbs)

Delavan Lot, Sleepy Hollow Cemetery (Photo: Adrea Gibbs)

It does seem, though, in spite of the overwhelming assets attributed to both Sleepy Hollow and Tarrytown, the Legend remains the featured attraction. While the local restaurants, shops, and sundry locations are considered “all in,” entities like Philipsburg Manor, Lyndhurst, Sunnyside (Irving’s home), Van Cortland Manor, not to mention Rockefeller National Park, while important sites and landmarks of the region, are, for the most part, supporting players. It is the promise of spirits and supernatural encounters that brings people to visit, which is exactly how the town positions its marketing. That and proximity to New York City which doesn’t hurt either.

People do want to know more about the Legend and how it relates to the community.  McCue said recently she had people visit from Poughkeepsie and found herself in a 20-minute conversation about the FOX show. On another occasion, she was talking about the church to a family from Los Angeles when she noticed a young woman, sitting quietly, who was wearing a medical necklace that stated “autistic.” After finishing her talk about the church history, McCue approached the woman and asked if she had come to Sleepy Hollow because of the Legend.

The woman lit up and began talking about the Burton film, of which she was a huge fan. McCue took her to the burying ground to show her the headstone of “Katrina” (Eleanor), which simply made this woman’s experience reach beyond her expectations. “I don’t know what it is about the Legend of the Sleepy Hollow that can reach out and grab the imagination of writers, directors, choreographers, animators and composers, but at that moment, I was grateful for Burton’s Legend because it provided a medium for this young woman to communicate to others.”

Perhaps Schweitzer put it best. “Washington Irving created ‘the brand’ of Sleepy Hollow more than 200 years ago, and Historic Hudson Valley has been extending that brand for many years. Our programming, such as The Great Jack O’Lantern Blaze, which alone draws 150,000 people, along with offerings from other institutions, is what really gives people a reason to come and spend time and money here.” There is an undeniable truth to that and when all is said and done, a visit to Sleepy Hollow, if specifically for the Legend, find Captain Kidd’s elusive treasure, visit the Rockefeller estate, Kykuit, which as an interesting side note, is one of the top cultural attractions in Westchester County, or any one of the credible reasons, no one will be disappointed. With it quickly approaching, most certainly autumn lends itself particularly well toward seeing the sights. One indisputable fact remains, regardless of interest or time of year, which is perhaps the most surprising of all to visitors. That Sleepy Hollow, Legend aside, is a tangible, inviting, thriving community.

Therein is the reality of Sleepy Hollow. This community is smart, playing to its strengths, and with Halloween being the second largest grossing holiday in the U.S., it only seems to reason they are positioned perfectly to take tactical advantage of the season. Economics aside, it is a bastion of historical and fictional wealth, well worth a day trip or overnight for anyone with even the slightest inkling of fascination.  Who wouldn’t want to take night tours in Sleepy Hollow Cemetery while carrying a stone lantern between headstones? Or traipse across the reconstructed bridge that is purportedly in the general area where Ichabod Crane met his demise? Or eat lunch at The Horseman Cafe?  There is something about feeling like you are walking in the steps of others, be it Revolutionary soldiers, fleeing slaves, or the fictitious Ichabod Crane, that is, simply put, appealing. You get to be a see a piece of the story, in a real place, in your own time, even if only on the periphery.