Statue of the headless horseman chasing Ichabod Crane
Haunted Travels,  New York,  The Archives

It’s October, Try Not to Lose Your Head

Man wearing a suit and carrying a briefcase with a jack-o-lantern on his head.

I don’t know about you but October is my FAAAAVORITE time of year. The air cools. The leaves fall. And the night time extends itself. For some, this is a sad time indicating the end of summer but for me…I get more excited with every pumpkin I see on my neighbors’ porches. Since I often have to remind myself “Look, it’s October, try NOT to lose your head.” I thought it would be fun to share with you the time we visited the Old Dutch Church graveyard…the stomping grounds of the Headless Horseman. So grab a pumpkin latte and let’s get spooky!

It all Happened in Tarry Town, NY

From the listless repose of the place, and the peculiar character of its inhabitants, who are descendants from the original Dutch settlers, this sequestered glen has long been known by the name of Sleepy Hollow…A drowsy, dreamy influence seems to hang over the land, and to pervade the very atmosphere.

– Washington Irving, “The Legend of Sleepy Hollow”

Wooded area with a fallen tree, brown leaves on the ground and green leaves on the trees
The Listless Repose

The story, set in the late 1700’s, takes place in the countryside around Tarrytown, New York. The area is reportedly haunted. Some residents claim the town was “bewitched” when it was founded. While others say the mysterious atmosphere is the result of a curse put upon it by a Native American Chief. Some of its residents experience mysterious and supernatural occurrences – like falling into trances, seeing strange sights and hearing voices and music “in the air”. The most famous of all these mysterious occurrences is the sighting of the Headless Horseman.

The Origin Story

Cannon overlooking a grassy area with a tree in the distance
Revolutionary Cannon in the Old Dutch Church Graveyard

The restless horseman is the spirit of a Hessian soldier lost his head during in the Revolutionary War. At night, he rides through the town to find it or to vent his rage.

The Legend Begins

White one room school house with a black roof, sitting in a field
“Ichabod Crane’s” school house

One summer, Ichabod Crane moved to the town to serve as their school master. Everything was going his way until the day he set his sights on Katrina Van Tassel, the daughter of wealthy farmer Baltus Van Tassel.

The Ghost Story

Statue of the headless horseman chasing Ichabod Crane
The Horseman

At the Van Tassel’s annual autumn party, rival suitor Brom Bones, decided to scare off Ichabod by sharing the story of the Galloping Hessian who rides a fiendish horse through the lanes of Sleepy Hollow, searching endlessly for his head. In his rage, he collects the heads of anyone he encounters before the bridge that leads to the burying grounds at Old Dutch Church.

Black and white image of a row of headstones leading to small stone church
The Old Dutch Church

After the party, Ichabod rode alone through the Hollow where he encountered a hulking figure on a horse. Whether it was Brom, playing a joke, or the Horseman, collecting another head, is all part of the legend. All that is known for sure was that Ichabod’s riderless horse was found the next day and the school teacher was never heard from again.

The Tarrytown Experience

We visited Sleepy Hollow and the Old Dutch Church burial grounds in May. While the covered bridge from the legend is no longer standing, they do have a placard showing where it was back in Irving’s time.

Blue metal sign that explains the covered bridge from the "Legend of Sleepy Hollow" stood on this site
The spot of the Horseman Bridge

About a quarter mile from that spot, a new wooden bridge spans the stream and provides crossing from the town into the cemetery.

Two women standing on a wooden bridge across a creek in a wooded area
Momma and Me

Though the terrain was a little challenging, we enjoyed walking through the 3 acre cemetery on our way to visit Washington Irving’s gravesite and we saw some interesting sites.

Fun Facts I HAVE to Share

In researching this article I found out some really fun things I thought you’d enjoy.

1. Ichabod Crane was a REAL Person

I wonder if Irving met Col. Crane somewhere in New York and liked the name so much he took it for his story.

2. The Character of Ichabod Crane was Based on a Real Person – Jesse Merwin

It turns out Irving and Merwin were friends back in Kinderhook, NY. I found out about him when looking for images related to Ichabod Crane. The school house where Merwin taught is now owned by the County and the school district has been renamed the “Ichabod Crane Central School District”. Pretty cool. I wonder if their mascot is the Headless Horseman?

3. William Rockefeller’s Father was a Snake Oil Salesman!

Old time photo of a man with a white beard and hair. Wearing a suit coat, a vest, and a banded collar white shirt
William Rockefeller Sr.

I wanted to be sure I cited the correct William Rockefeller’s grave in the Old Dutch Church cemetery and inadvertently fell down a rabbit hole. Turns out William Rockefeller Sr was a bigamist, a rapist and a FOR REAL snake oil salesman! His son, William Rockefeller Jr., was the co-founder of Standard Oil and is buried in Sleepy Hollow’s cemetery

As the Mummy said…that’s a wrap!

Oh how I LOVE October and Halloween! I hope you’ll stay turned for our upcoming Haunted Travel articles and we would LOVE it if you shared about us with your friends. They can subscribe to us for free get weekly newsletters with new articles and curated content. And they can follow us on Instagram at The__Travel__Oracle for real time adventures.