Visit Sleepy Hollow the Legendary Home of the Headless Horseman

From Books to Blockbusters

Visit the Real Sleepy Hollow


 

Driving through Irvington I couldn’t help but notice that the clear blue sky had somehow turned grey. I always admired the brightness of the fluorescent yellow leaves against a grey sky, but nestled at the bottom of Washington Irving’s tombstone they look even prettier. I was in Sleepy Hollow, home to the legend of the Headless Horseman and neighboring village to Washington Irving’s home of Irvington, NY.

An actual street sign in Sleepy Hollow. The entire town has signs like these. How cool is that!

An actual street sign in Sleepy Hollow. The entire town has signs like these. How cool is that!

Regarding Tarry Town, NY

Not far from this village, perhaps about two miles, there is a little valley among high hills which is one of the quietest places in the whole world. A small brook murmurs through it and, with the occasional whistle of a quail or tapping of a woodpecker, is almost the only sound that ever breaks the uniform tranquility. From the listless repose of the place, this sequestered glen has long been known by the name of Sleepy Hollow.”

– Washington Irving, American author of The Legend of Sleepy Hollow 

Washington Irving's Headstone at the Sleepy Hollow Cemetery

Washington Irving’s Headstone at the Sleepy Hollow Cemetery

This is a region along the Hudson River where steep hills collide with stones. As different as it may be from the Sleepy Hollow of 1820, the legend is very much still alive and thriving. Where there were once just hills, pastures and forest, there now lies homes and local businesses. Layered above Phillipsburg Manor (site of the annual Horseman’s Hollow Halloween attraction and mentioned in the Irving’s story as a place where Ichabod Crane would frequent), lies the Old Dutch Church, a well preserved snapshot of the past.

The Old Dutch Church is mentioned in Irving’s story as the purported haunt of the Headless Horseman, and where the people that inspired the characters in the story are buried. Adjacent to its graveyard is a burial ground, not to be confused with where Washington Irving is buried. The Old Dutch Church of Sleepy Hollow and its burying ground are the setting for Washington Irving’s short story “The Legend of Sleepy Hollow.” Irving himself is buried in the south end of Sleepy Hollow Cemetery, overlooking the grounds of the Old Dutch Church. the Sleepy Hollow Cemetery, the final resting place of Washington Irving. Just a 10 minute drive from here you can find Sunnyside, Washington Irving’s Estate alongside the Hudson River.

Sleepy Hollow

The whole neighborhood abounds with local tales, haunted spots, and twilight superstitions.

-Washington Irving, the Legend of Sleepy Hollow

Horseman's Hollow, Sleepy Hollow's annual Halloween terror event, photo by Hudson Valley

Horseman’s Hollow, Sleepy Hollow’s annual Halloween terror event, photo by Hudson Valley

Everywhere you turn in Sleepy Hollow you are reminded of the legend that lives there. From street signs decorated with the Headless Horseman, to tour guides dressed in period clothing and even a sculpture in the city’s center. The Headless Horseman lives everywhere, hiding, creeping, much like he did in the Legend of Sleepy Hollow.

Sleepy Hollow statue of the Headless Horseman on Route 9

Sleepy Hollow statue of the Headless Horseman on Route 9

Police cars in Sleepy Hollow proudly honor the legend.

Police cars in Sleepy Hollow proudly honor the legend.

State acknowledgement of the legendary sites.

State acknowledgement of the legendary sites.

Sleepy Hollow is a place that will enrich you with the culture of American literature and folklore. It is a must see Fairytale Destination for all ages. If you are heading to Sleepy Hollow, a great time of year to go is the early fall (first week in October). This is a lovely time of year in this part of the U.S. and there are loads of Halloween events that won’t be too crazy this early in the month. I highly recommend staying at the Castle Hotel & Spa just 10 minutes away with stunning fairytale accommodations in an actual castle.

The legend himself making an appearance at Horseman's Hollow, photo by Bryan Haeffele

The legend himself making an appearance at Horseman’s Hollow, photo by Bryan Haeffele

Planning to Visit Sleepy Hollow?

Visit Sleepy Hollow

Hudson Valley (for events and attractions)

Castle Hotel & Spa

The Legend of Sleepy Hollow Places

Old Dutch Church of Sleepy Hollow and Old Dutch Burying Ground

Sunnyside

Philipsburg Manor

Sleepy Hollow Cemetery

Halloween in Sleepy Hollow

Horseman’s Hollow

Irving’s ‘Legend’

The Great Jack-O-Lantern Blaze

As always your thoughts are well received. Happy Fairytale Travels!


About Christa Thompson

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Christa Thompson is the Founder and Senior Editor of The Fairytale Traveler. Christa has been traveling the world since 2003 when she attended a summer abroad study at the University of Cambridge in England. Since then, her wanderlust has been fierce. Her three passions in life are her son, traveling, and being creative. The Fairytale Traveler brand gives Christa the opportunity to do all of these things and to live intentionally every day.

“It’s never too late to believe in what you love and to pursue your dreams.” -Christa Thompson

7 Comments on this post

  1. […] a 6 hour road trip from Sleepy Hollow where I was scared out of my socks at the Horseman’s Hollow event, I was ready to relax and […]

  2. Great blog! I didn’t even realize that there was a town dedicated to the headless horseman. Would definitely need to check out it if I’m ever in the area.

    Steve / Reply
  3. Hey there! Do you use Twitter? I’d like to follow you if
    that would be ok. I’m definitely enjoying your blog and look forward to new
    updates.

    Lien / Reply
  4. […] for this time of year (Halloween) I stumbled on the page associated with the Legend of Sleepy Hollow in upstate New York. Christa provides a short excerpt from Washington Irving’s The Legend of Sleepy Hollow and then […]

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