Have you ever found yourself in a place so ethereal that you felt you were walking a tightrope between a fairytale and the real world happening around you? While The Legend of Sleepy Hollow is a work of fiction, the setting of Tarrytown is as real as the Headless Horseman was to Ichabod Crane.

Shortly after declaring independence from England in 1776, the United States found itself an infant country with meager resources but brimming potential and overflowing dreams of what could be. Although the colonies were influenced by their origins, it was now up to the citizens to create a new culture that was uniquely their own. American art would have to be painted, drawn, and sculpted, American music composed, and American literature written for the first time. 

Before Mark Twain took us on adventures with Tom Sawyer or Edgar Allan Poe penned a poem, and long before John Steinbeck taught us about our human nature in East of Eden, there was Washington Irving.

Born to immigrant parents in 1783, Washington Irving was among the first generation of those born in the newly formed United States. He was raised in a modest home, the youngest of 10 siblings, in Manhattan, New York. When Irving was a boy, it’s been said that he wasn’t much interested in school and would often sneak away to take dance lessons or go to the theater. It’s ironic considering the first time I would ever hear about Washington Irving would be in school when my third-grade teacher read us his story, Rip Van Winkle.

I can’t help but wonder how growing up in a family that large, in a city, that big, shaped the appreciation he would have for the quiet village of Tarrytown (his eventual residence and the setting for The Legend of Sleepy Hollow.) He describes the small New York community in The Legend of Sleepy Hollow by writing: “If ever I should wish for a retreat, whither I might steal from the world and its distractions, and dream quietly away the remnant of a troubled life, I know of none more promising than this little valley.” 

Having had the opportunity to visit several times, I can attest that the “drowsy, dreamy influence that seems to hang over the land,” that Irving writes about is very real, particularly when the air turns crisp and the trees drop their orange leaves. It sits right on the Hudson River and encompasses everything the Northeast should be in Autumn. 

The village has changed since Irving lived there. Electricity has been installed, horses and buggies have been replaced with automobiles, and the population has since more than quadrupled, but the enchantment that The Legend of Sleepy Hollow has created is alive and well.

The residents have completely embraced the legend. The local high school has adopted the “horsemen” as their mascot, the main street is bedecked with orange and black street signs year-round, and North Tarrytown has since officially changed its name to Sleepy Hollow.

Washington Irving spun a tale so intriguing that the locals honor the story with a host of different events each Halloween season. You can visit the final resting place of Washington Irving at the Sleepy Hollow Cemetery and see the Old Dutch Church that Ichabod Crane was so desperately racing toward to escape the clutches of the Headless Horseman. You can attend the Great Jack O’ Lantern Blaze where you’re able to view over 7,000 carved pumpkins. If you’re really wanting a good spook, you can listen to a master storyteller’s recitation of The Legend of Sleepy Hollow during the month of October at Washington Irving’s historic cottage estate. 

The village of Sleepy Hollow is magical, but the reason for its bewitching charm is owed to Washington Irving. When a young nation was figuring out how it would portray itself to the world, Irving used his gift of writing to become one of the first American authors to be globally recognized. I’m sure he had no idea or even the intention that centuries later a town of people would pay annual homage to his story or that groups of listeners would huddle close together to hear live retellings about the Headless Horseman.

It has caused me to contemplate how I can create the same magic and wonder in my home and family that Washington Irving was able to do in Sleepy Hollow. What traditions can I start that will embody Halloween? What worthwhile activities can I do with family or friends that will create an entrancing atmosphere that they look forward to with each passing year?

For me, I think I'll start with the very thing that raised this desire. I’ll turn off the lights, gather around flickering candlelight and grab a copy of The Legend of Sleepy Hollow to read of the drowsy village on the Hudson River and Ichabod Crane’s chilling encounter with the Galloping Hessian of the Hollow.

Create magic in your home this Halloween by reading one of our many frightening stories such as Dracula, Frankenstein, or Roald Dahl’s Book of Ghost Stories. Play a haunted game with our bone dominos set, or hang a bat garland on your porch and let them flutter in the October breeze. Not only is October the month of Halloween… it’s also Family History Month. Shop our Halloween tradition that delights and educates your real family "ghosts"-- your ancestors.


Stay tuned for a mini travelogue for some of our favorite places to stop, stay, and eat in upstate New York. If you have never been, plan a trip to immerse yourself in the Hudson River Valley. 

September 09, 2022 — Tyler Johanson


Christine said:

I live very close and have been visiting Sleepy Hollow since my childhood. I adore the tale of the Horseman and the lore of this beautiful town. My children have grown up to admire all things Sleepy Hollow, so much so my son lives here. Such a magical and beautiful place for all seasons!

Monica said:

Ha! We live in Tarrytown! My kids are Sleepy Hollow Horsemen :) October is a busy month for us, as you can imagine. We locals know the backroads to take and let me tell you – every day I take it all in and think how lucky I am to call this place home.

Katie said:

We are heading there in two weeks’ time – our second visit. I can’t get enough and look forward to your travel recommendations! xo

Becca Lloyd said:

We loved visiting this place during Halloween season while living on the East Coast. They had the most incredible pumpkin display, The Blaze! I learned the most efficient pumpkin-carving techniques during our visits!

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