Three Sleepy Hollow Things Not in Sleepy Hollow

September 16, 2021 — I’ve taken you to Sleepy Hollow many times here on OTIS. I’ve also taken you beyond it to Kinderhook, New York (Sleepy Hollow North), which has a strong connection to Washington Irving and his Legend characters. I’ve taken you to Manhattan, with its Sleepy Hollow-themed bar and erroneous historical plaque about Irving. I’ve taken you to Sleepy Hollow, Illinois, and to Sleepy Hollow, Wyoming. To Staten Island where Ichabod Crane’s namesake is buried. To my bathroom, which is Sleepy Hollow-themed. Anywhere where the Headless Horseman rears its…horse’s head.

And I have more Sleepy Hollow for you. I will always have more Sleepy Hollow for you.

The Headless Horseman Pursuing Ichabod Crane (Washington, D.C.)


How many monsters have been enshrined in the Smithsonian? I don’t know. Not many, I’m guessing. At least not as proudly displayed as the Headless Horseman.

On a wall of the Smithsonian American Art Museum is an oil painting by John Quidor of the Headless Horseman pursuing Ichabod Crane. It’s called The Headless Horseman Pursuing Ichabod Crane. You know the image. It’s a classic American one. The terrified Crane. The black rider, his neck stump shrouded ambiguously in the mane of his steed. The creepy Fall feel with tree limbs like lightning bolts. The Old Dutch Church and Cemetery a tiny beacon of hope in the background. Creepy owl that you didn’t know about until now. Quidor painted it in 1858, 38 years after the story was published and less than a year before Washington Irving died.

Creepy owl.

But this wasn’t Quidor’s first brush with Sleepy Hollow. In 1828, eight years after The Legend’s publication, he painted Ichabod Crane flying from the Headless Horseman. He called it Ichabod Crane flying from the Headless Horseman. It’s not as classic an image as his 1858 painting, mostly because it doesn’t feature the Headless Horseman. That painting is at the Yale University Art Gallery, but not on display when I visited a while back. And that’s fine. I didn’t lose my head over it.

Also, I’m right now putting together a pitch for “Finding Monsters in the Smithsonian,” a short-run docuseries starring me as the host. Hit me up, producers.

The Grave of Ichabod Crain (Surry, New Hampshire)

This is how crazy I can get for The Legend of Sleepy Hollow: Visiting a grave that has nothing to do with the story, the author, nor the legend, only because it bears a name similar to Ichabod Crane. Ichabod C-R-A-I-N. That’s it.

And, actually, Ichabod C-R-A-I-N might actually have been a C-R-A-N-E. Both spellings appear on historical documents. Too bad the latter didn’t end up on his grave. Then probably more than just me would have dropped by in the past 150 years. But if you still want to, the grave is in a cemetery behind Surry Town Hall in Surry, New Hampshire. 

Either way, this real-life Ichabod C. died in 1866 at the age of 82, meaning The Legend had already become a classic that he was possibly aware of.

Ichabod Crane Highschool (Valatie, New York)

Ichabod Crane Highschool is about two hours north of Sleepy Hollow, so on the Kinderhook side of the story. The school’s mascot is Ichabod Crane as the Rider, a generous description of Crane’s horsemanship. The Riders have a great logo, and a quote from Irving is etched into the school’s facade. It sounds like one of those misattributed quotes thrown around the socials all the time, and maybe it is. I can’t quite find the source, possibly because the Google results are an overwhelming tide of quotation collections and motivational websites. I assume the school did its homework, though.


The building probably has more Washington Irving references inside, but strangers aren’t allowed to just walk into schools. I’ve learned.

I am told that the Riders do not compete with Sleepy Hollow’s high school, the mascot of which is the Headless Horseman. Which is too bad. They should. The Riders vs. the Horsemen. They could call it the Bridge Match, paint a jack-o-lantern face on the ball (especially if it was a basketball). Even if it was only an October exhibition game.

Also I’m writing, “The Riders vs. the Horsemen” as a live-action children’s movie. Hit me up, producers.