Hang Onto Your Head! Things To Do In Sleepy Hollow NY

by | Oct 15, 2021 | Destinations, Family Adventures, North East, Traveling with Teens, USA, Weekend Trips

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My first reaction when I found out Sleepy Hollow was a real place was stunned disbelief. “No way!” I thought, instantly curious. But friends, the famed Sleepy Hollow from Washington Irving’s infamous story, “The Legend of Sleepy Hollow” about the Headless Horseman is a real town on the eastern bank of the Hudson River, about 25 miles north of Midtown Manhattan in New York City, called Terrytown!  I don’t know how I missed it because as l investigated deeper, it turns out it’s the perfect fall getaway! Especially if you’re into haunted history!



PIN - While the legend of the headless horseman might not be real, the town of Sleepy Hollow definitely is! And it's the perfect fall getaway! - Things To Do In Sleepy Hollow NY


Legend of Sleepy Hollow Story

In case you’ve never read the book, I’ll give you the cliffs notes version. Ichabod Crane, the local schoolteacher, lives in Sleepy Hollow NY, an area known for being haunted by a ghost horseman who, you guessed it, lost his head in an unspecified battle. Legend has it that the Headless Horseman cannot cross a bridge located near The Old Dutch Church. Ichabod finds himself competing with the local troublemaker, Brom Bones, for Katrina’s hand in marriage. She’s kind of a big deal, one of the prettiest girls in town. One night Ichabod is riding home alone late at night when he comes upon a silent, spooky, fellow horseman. Then Ichabod realizes, “Oh wait, this guy doesn’t have a head” and he takes off riding for the bridge. According to the legend, Ichabod makes it to the bridge, but the Headless Horseman flings his severed head at him, Ichabod doesn’t manage to duck and the next morning, well, there’s just no trace of Ichabod. He’s just vanished. Washington Irving left what happened to Ichabod up to the reader’s interpretation, but there are two commonly accepted theories. 1. It’s highly implied that Bones, a skilled horseman, dressed up like the Headless Horseman to scare the pants off Ichabod and get him to flee town. Or 2. Bones straight up murdered Ichabod. Either way, the story is a fun, spooky American legend that has been turned into movies, theatre, TV shows, cartoons, and even a postage stamp. 


Sleepy Hollow Attractions


Old Dutch Church 

church, sleepy hollow - Things To Do In Sleepy Hollow NY

Old Dutch Church is actually a real place you can visit! It’s the oldest church in New York. Photo Courtesy of Daniel Case via Wikimedia.


Yes, The Church from the legend is a real place you can really visit. You can also pay your respects to Ichabod at the bridge where he was allegedly run out of town. It’s more of a tourist attraction now than a working church. Services are only held during summer months. The church was built around 1697, and in the 1990’s the congregation funded various restoration projects to restore the church and get it listed on The National Register of Historic Places. 


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Sleepy Hollow Cemetery

headstones, cemetery - Things to do in sleepy hollow, ny

The final resting place of Washington Irving, the man who made Sleepy Hollow famous. Photo courtesy of James P Fisherill via Wikimedia.


Sleepy Hollow Cemetery is the final resting place for many famous people, not just our favorite author, including Andrew Carnegie, several members of the Rockefeller family, members of Alexander Hamiliton’s family and many more. During the fall, the cemetery offers several different historical tours to choose from. I highly recommend a tour, as the cemetery is several hundreds of acres large, and therefore a little big to navigate on your own. 



house, estate, sunnyside - Things to do in sleepy hollow, ny

If my house was this nice, I probably wouldn’t get any writing done. Photo Courtesy of Ken via Wikimedia


Washington Irving’s Estate, Sunnyside, is open to visitors on weekends in the fall. The Irving family lived there until 1945 when the Rockefellers purchased the property and restored it as part of an effort to maintain historical sites along the Hudson Valley. 

Sunnyside is furnished with many of Irving’s original furniture, including most of the pieces in his study where he did his writing. 



Be sure to get your tickets for Sunnyside ahead of time. They are not sold at the door. 


Not going to make it to New York anytime soon? You can visit a replica of the outside of Sunnyside in Liberty Square at Walt Disney World’s Magic Kingdom Park. 


Ghost Tours

Irving said in his book that Sleepy Hollow was “unusually haunted.” Maybe that’s why there are more ghost tours available than I can count! From tours that focus on Headless Horseman legend to tours that focus on ghost sightings by local residents and everything in between, if ghost hunting is your thing, you have plenty to choose from! If you don’t have time for an escorted tour, the locals say that the town theatre is especially haunted. That might be a good place to do your own ghost hunt. 


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Great Jack O Lantern Blaze

jack o lantern, pumpkins

I’ve never quite mastered making Jack O Lanterns, maybe I can get one of those volunteers to show me a few tricks. Photo Courtesy of David Menidrey on Unsplash


The Great Jack O Lantern Blaze features over 7000 pumpkins, hand-carved by over 1000 volunteers! It’s a walk-through event, and you can enjoy many special displays like a New York City skyline and a Hudson River display. Blaze is held on select nights in the fall. 


When You Go



Getting To Tarrytown From Los Angeles

Since Tarrytown is only an hour outside of New York City, you could easily use NYC as your base and do a day trip to the area. Public Transportation in Tarrytown is slim. You’ll need to rent a car or plan to Uber. Many of the places in this story are only open on a very limited basis year-round, so if you plan to visit outside of the Halloween season, call ahead to make sure your intended destinations are actually open. I highly recommend securing tickets well in advance. 

An excellent discount site for flights (and cars, hotels) is Expedia! This is where we start our research for the best deals!


To get discounts on tours in the area, we recommend Get Your Guide or Viator (which offers 51% off last-minute tours!).


Where to Stay In Sleepy Hollow

There is a really cool estate, right on the Hudson, where you can rent a room. When in Rome, right? You can sip your coffee and pretend like you’re writing the next great American novel. There is also the Sleepy Hollow Hotel with views of the Hudson River within walking distance to everything. If you want to travel on points, here’s a good Marriott and a Courtyard Marriott in the area to choose from.



While the legend of the headless horseman might not be real, the town of Sleepy Hollow definitely is! And it's the perfect fall getaway! THINGS TO DO IN SLEEPY HOLLOW, NY


Emily Householder Stacey is a travel agent and writer based out of Carnation City, Alliance Ohio. She is a certified chicken who sleeps with the lights on, and therefore doesn’t really like ghost stories, but she has seen 2 actual ghosts. Neither of them were headless.