The Hunt for the Headless Horseman

Sleepy Hollow & Tarrytown, New York

Although I now refer to soda as “pop,” easily slip into a distinct Midwestern twang, and live close to cornfields, the foremost part of my childhood was spent in northern New Jersey.  Growing up, I was surrounded by early American history.  My town was colonial; I lived close to important sites from the Revolutionary War.

And what I distinctly remember was the stories of Washington Irving: staples of early Americana like “Rip Van Winkle” and “Sleepy Hollow and the Headless Horseman.”  The Hudson River Valley he wrote about wasn’t too far away from me.  The Dutch settlers?  Some of my classmates were descended from them.

So during a crazy winter break in December of 2015 in which I ventured to Connecticut, New Jersey, NYC, and Washington, D.C. and was first exposed to what driving is like on the East Coast (in short: pure hell), I couldn’t help but venture to the mystic places of those long-ago stories I’d grown up reading.

Here’s how it happened: I was driving down from Connecticut to New Jersey with the plan to cross the Tappan Zee Bridge when I realized how close I would be to Sleepy Hollow and Tarrytown, New York.

Of course I had to go!

Tarrytown and Sleepy Hollow are small villages located side by side overlooking the Hudson River.  Both were founded in the 1600s (which is still a bit surreal to me after living 15+ years in the Midwest, where the average town was founded more than 200 years later) and appeared to truly be villages in the sense of the word.  Small downtowns, local shops and restaurants, town parks — even village notices, for goodness’ sake.

I’d been a bit afraid that they would be turned into the McMansion-filled urban sprawl a lot of northeast towns have become, but I was pleasantly surprised by what I found.  It felt as if they’d retained their Dutch settler origins — quite refreshing.

I drove down what appeared to be the main thoroughfare of Broadway until I came upon Sleepy Hollow Cemetery, burial ground of Andrew Carnegie, William Rockefeller, Elizabeth Arden, and, of course, Washington Irving!

Irving had recently come back on my radar.  Earlier that month, I’d traveled to Spain because I was turning #dirty30 and obviously wanted to do it in style, and while spending a few days in Seville, I’d discovered that he had actually been an ambassador there and written a few books about the history of Spain.  It seemed like too much of a coincidence, and I knew I had to pay him homage.

Thus: the cemetery.

It was rainy and gray outside when I arrived in the cemetery.   With a map in hand, I started driving through it, looking for the famous graves.  I found the Rockefeller mausoleum and, at last, Irving’s grave.




It was quite strage, especially since I could see the Hudson River down in the valley—as if I’d encountered a piece of my childhood.

I snapped a photo of Irving’s grave with awe, then drove down past the Headless Horseman Bridge (!), where, unfortunately (okay, fortunately), no ghosts were to be found.


Later, as I sat in a hipster coffee shop in Tarrytown, drinking a ridiculously overpriced froo-froo #basicbitch caffeinated beverage and reading Growing Up Jung, I realized I was relaxed, calm, and happy—and that this would be a short foray I’d look back on fondly.


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