Spooky Autumn Nights in Sleepy Hollow, New York

By Contributing Columnist, Nicole Bergstrom

Posted on 4 min read

Hi everyone and Welcome back to the Travel Section of The Code of Style Magazine, and I’m delighted to share with you this post about “Spooky Autumn Nights in Sleepy Hollow”, by our Contributing Columnist, Nicole Bergstrom.

I’m Julia (Instagram: @julia.rees_), Senior Managing Editor for The Code of Style. I hope you enjoy this article about Sleepy Hollow and I’ll be back to share some more travel inspiration with you again soon! 

So, read on to find out more about “Spooky Autumn Nights in Sleepy Hollow” from Nicole.

I grew up in the northeast region of the United States and for 15 years I lived in the Lower Hudson Valley in New York state. Autumn has always been my favorite time of the year. I loved it especially in this area when the leaves on the trees are changing to brilliant shades of red, orange and yellow. My family and I spent many weekends at pumpkin patches and apple picking at local orchards. The area is also rich with early American history as New York was one of the original 13 colonies. 

A Dutch Colonial Settlement Near the Hudson River

In this area is a little hamlet that used to be known as North Tarrytown, but since 1996 has taken back its old name of Sleepy Hollow. This quaint little town is located 30 miles north of New York City. If you are visiting the city during the month of October, it is worth the quick drive or train ride on the Metro North Railroad to this little village for the festivities. 

This little hamlet is the location that inspired Washington Irving to write The Legend of Sleepy Hollow.  First published in 1820, this short story celebrates its 200th anniversary in 2020.

Sleepy Hollow

Many of the characters in “The Legend of Sleepy Hollow” were based on people that Washington Irving knew at the time he lived there. A favorite pastime of the residents was to spook and thrill each other with tales of ghosts in the area.

Many of these real-life people are buried in Sleepy Hollow Cemetery including the Van Tassels and even author Washington Irving himself. 

Sleepy Hollow

In the center of the village visitors can explore Philipsburg Manor and see some of the structures that existed long ago during the colonial period. You could make a reservation for a walking tour operated by the local Historical Society to learn more about the area. Tours are also available for Sunnyside, the estate in nearby Tarrytown where Washington Irving lived. 

Legends Weekends in October

Since 1996 Sleepy Hollow has had Legends Weekend. During the month of October when the foliage is peaking, Sleepy Hollow and the surrounding area are full of activities that commemorate the sights, tastes and sounds of autumn, Halloween and Irving’s classic work.

Two National Historic Landmarks, the Old Dutch Church and Philipsburg Manor House are located here and are part of the autumn festivities.

Irving’s Legend 

Sleepy Hollow

In this event located inside the Old Dutch Church, an actor dressed in colonial costume orally recites The Legend of Sleepy Hollow for the small audience. The spectators are treated to sound effects, a touch of humor and accompanying organ music that sets the perfect eerie mood for the story.

This event is located in the exact church from the tale and the churchyard the Horseman rises to stalk Ichabod Crane. Just a few feet from this church is the bridge where Crane disappeared. 

Horseman’s Hollow

Spooky Hollows

This event is the highlight of the autumn season in Sleepy Hollow. You enter the event by walking on a pathway through the woods illuminated by lanterns and populated with signs that have ominous warnings about curses and the haunted village. Once you get inside, you are transported back in time to America during the colonial period at Halloween time.

Sleepy Hollow
Sleepy Hollow

On the grounds of Philipsburg Manor, there are food vendors serving traditional autumn fare such as hot cocoa, apple cider and pumpkin flavored treats. There is also live entertainment throughout the site. Many actors in costume are present to jump out and scare the visitors while they make their way through the haunted village.

Spooky Hollows
Sleepy Hollow

Finally, you arrive at a stable and barn where you see the Horseman himself. If you dare to let him get close enough, he will try to grab you and take your head!

Sleepy Hollow

Some of the other popular events occurring at this time include The Great Jack O’ Lantern Blaze, where thousands of illuminated carved pumpkins are on display.  Sleepy Hollow Haunted Hayride and Block Party is where you can ride the route that Ichabod Crane traveled as he fled the Hessian Horseman. After the ride, the free block party has live entertainment, children’s activities and food vendors. 

Spooky Hollows

The events draw thousands of people to Sleepy Hollow during the month of October. Due to the pandemic, some of the Halloween events at Sleepy Hollow have been assigned limited capacity , while others such as Irving’s Legend and Horseman’s Hollow have been cancelled.

Hopefully in 2021 the town will be able to resume its full schedule of autumn festivities. The Halloween season during America’s Colonial period is something that should be enjoyed by all.  The future generations should experience how fun a live reenactment of one of the best examples of early American literature can be.

I hope you enjoyed this article about Sleepy Hollow and I can’t wait to share some more travel inspiration with you again soon! 

Julia x ( Senior Travel Editor)

Nicole Bergstrom is a freelance travel and lifestyle journalist. Follow Nicole on her journeys at Nicole the Travel Scribe.

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Spooky Autumn Nights in Sleepy Hollow, New York