Ever wanted to walk the streets that Ichabod Crane and the Headless Horseman once stormed through? Experience history as an immersive experience filled with hauntings and captivating stories. Sleepy Hollow is known for its spooky Halloween events. Many of these events feature the famous story of Ichabod Crane and the Headless Horseman. Yet, many don’t know the more hidden history of the rather gruesome André tree.
The local residents of sleepy hallow know how to go all out. During Halloween, there are endless events and activities for all fright and non-fright lovers. This spooktacular town has a little bit of everything, so if you’re wanting to visit for Halloween, keep reading to find out how to plan the spookiest trip possible!
Legend of Sleepy Hollow
Washington Irving’s 1819–1820 work The Legend of Sleepy Hollow portrays Ichabod Crane, a pompous schoolmaster. He is in love with Kartina Van Tassel, the daughter of a wealthy and powerful landowner. It’s said that Katrina used him to make her lover jealous. Brom Bones posing as the headless horseman scares him away with a cunning plan to pursue him into the woods at night.
The Headless Horseman, who is also known as the Galloping Hessian, is often shown riding a black horse and carrying a pumpkin. Like a Jack-o-Lantern. Ring any bells? Though, in this version, the Headless Horseman is the specter of a Hessian soldier killed by cannon fire during the American Revolution.
Whether it’s Brom Bones or a headless Hessian Soldier, he’ll keep on living in The Legend of Sleepy Hollow. If you’re feeling really bold then consider visiting the Sleepy Hollow Cemetery. It’s the location where the ghost is claimed to have hitched his horse to the tombstones before setting out at night to find his severed head. Who knows maybe you’ll meet him there.
You get to decide whether it’s Brom Bones or the Hessian Soldier haunting Sleepy Hollow. .
Infamous Deeper History of Sleepy Hollow
Though Washington Irving’s narrative of the Headless Horseman has spread around the globe, Sleepy Hollow also contains a lesser-known Revolutionary War legend – André’s Tree.
There is still a role for Ichabod Crane and the Headless Horseman in this narrative, but an important part is missing.
The André’s Tree
Before Ichabod met the Headless Horseman on his last voyage through Sleepy Hollow’s hills and streams, he was shocked by the spectral energy that swirled around a ginormous tree.
A tree so large and massive that it was unlike any other tree ever seen, mingled with reverence and superstition. It had a trunk as tall as 111.5 feet. The branches extend forth for another 80 feet or more on each side.
Major John André Tragic Story
The tragic tale of a British intelligence officer, Major John André. He was arrested for being a spy and executed after being captured with
evidence of his crimes packed inside his boots. It’s important to note, he was only apprehended at Sleepy Hollow and his arrest site is still open to tourists. But what many don’t know is he did not die there.
André was reportedly beheaded on October 2, 1780, coincidentally, the same year Irving’s narrative is set. Before André drew the noose around his neck, Dr. James Thacher observed him take a white handkerchief out of his pocket and bandage his own eyes, bringing tears to the eyes of thousands of witnesses – making you wonder, if he was a spy and traitor, how were so many crying out for him?
Located in Patriot’s Park on Route 9, this 1853 monument was dedicated by “the people of Westchester County.” Historical documents from the nineteenth century indicate that the tree was linked to André. His name was included in the New York Travelog before James Kirke Paulding’s incorporation of the magazine in 1928.
The famous tale by Irving may have been inspired by his observation of this tree, although according to Paulding, it had been destroyed by lightning some 20 years before Irving wrote his famous story of Sleepy Hollow – so, what really happened?
So, given that the well-known story takes place in 1790, could it be that Ichabod ran into the tree’s twisted branches? Perhaps he harbored secrets of another world, just before he met his end at the hands of the Headless Horseman?
What occurred to Major André, Ichabod Crane, and the Headless Horseman was shrouded in mystery despite the abundance of evidence and conflicting accounts.
What To Do In Sleepy Hollow This Halloween
There are so many Halloween events in Sleepy Hollow, NY during the fall that you’ll want to keep coming back every year. It’s only a quick 30 miles north of New York City so you have to stop by for a trick.. I mean a treat.
Speaking of treats, here are my top best dessert spots that New York City has to offer!
Keep scrolling to find out my favorite Sleepy Hollow Halloween events. 
1. Sleepy Hollow Haunted Hayride
Looking for a little scare for your night? Climb aboard the Sleepy Hollow Haunted Hayride and get ready to be spooked as you follow the path Ichabod Crane took through the town of Sleepy Hollow. Make sure you have your eyes peeled for the Headless Horseman while you ride through the town and be prepared to scream when you enter the woods where you might just get a little fright. The fun doesn’t end in the woods through, the hayride continues on and ends in the cemetery, make sure you remember which path the Headless Horseman took, you won’t want to run into him on your way back.
2. The Great Jack O’ Lantern Blaze
Looking for something the whole family can do without the worry of being too spooked? Look no further! This is the biggest Halloween event Sleepy Hollow has to offer. There are over 1,000 volunteers who contribute their time scooping, carving, and lighting the pumpkins.
Not all Halloween events need to be scared-out-of-your-mind creepy, especially if you’re planning to do other eerie events later. The Great Jack O’ Lantern Blaze is a family-friendly event for all ages with over 7,000 jack o’ lanterns hand-carved, sound effects, and light shows. Most nights sell out so make sure to get your tickets as soon as possible!
3. Cemetery Tours
Visiting Sleepy Hollow’s 90-acre cemetery is a must for all who come to visit. Perfect for all history lovers, sculpture fanatics, and anyone who enjoys pretty scenery. You can’t visit Sleepy Hollow during Halloween and not book a cemetery tour.
Come see where legends Washington Irving, Andrew Carnegie, and William Rockefeller are buried and learn some history about their lives.
Looking for more fright in your tour? Book a two-hour lantern tour filled with murder, mayhem, and ghost stories. Learn about a true story of a multi-state police chase after a horrific murder of 5 young children and listen to ghost stories that bring an extra level of spook to the cemetery.
This specific tour is not intended for audiences under 18 years old.
You can book your tour here – you will not want to skip this.
4. Oktoberfest
Oktoberfest is an annual German celebration of the marriage of King Louis I to Princess Therese von Sachsen-Hildburghausen. Unlike the name suggests, Oktoberfest (both in Germany and in Sleepy Hollow) is celebrated in September rather than October.
So if you enjoy drinking beer, eating delicious German food, and want to dance to some Bavarian music without having to go across the pond, come celebrate Oktoberfest in Sleepy Hollow with local eateries.
Don’t drink or worry about bringing kids along – there is hot chocolate and cider offered too!
5. Tarrytown Halloween Parade
This Halloween parade consists of homemade floats, marching bands, and various entertainers such as stilts performers and magicians, all led by the Headless Horseman himself. This event is a fun and free event for the whole family. It starts at Patriot’s Park and runs all the way to Tarrytown’s Main Street.
Fun Fact: Patriot’s Park is where Ichabod Crane first spots the Headless Horseman.
After the floats and entertainers finish, there is a block party on Main Street. Come and celebrate the end of the parade with the band, DJ, and professional dancers. Food trucks and merchants along Main Street set up dinner tables on the sidewalks to ensure you don’t miss a thing!
6.Hulda’s Night At Rockefeller State Park Preserve
The Rockefeller State Park is home to seasonal activities. During warm weather, this includes activities such as hiking, running trails, fishing, and horseback riding. When the weather gets colder in the winter many participate in snowshoeing, sledding, and cross-country skiing. But during Halloween time – expect some spooky thrills.
Want to step back in time and get a taste of what Sleepy Hollow was like back in the day?
Your group will follow a path lit by lanterns into the woods. There you’ll join a traveler around a campfire and listen to local legends. After learning of the local legends, you’ll hear from the Pastor of a nearby church. The Pastor will recount how Hulda, the witch, threatens the flocks nearby. Once the moon rises it is time to finish the trek down to Hulda’s hut. There she will tell you the story of how she came to be.
Are you ready to experience old-time Sleepy Hollow? Grab your tickets here for only $28! 
7. Home Of The Legend & Irving’s Legend
This family-friendly event includes a tour of Washington Irving’s house, an original puppet show, and lawn games for the whole family. Come for the tour, stay for the performance of a lifetime – master storyteller Jonathan Kruk is performing Irving’s Legend under the stars, and who knows, maybe the Headless Horseman himself may make an appearance.
Tickets for the tour of the Legend
Tickets for Jonathan Kruk’s performance of Irving’s Legend
What To Expect In Sleepy Hollow
There aren’t any hotels in the town of Sleepy Hollow itself but rather in the town next door, Tarrytown. This being said, there are a variety of options to choose from when deciding where to stay and how to get around.
Where To Stay
Depending on the experience you want from your visit to Sleepy Hollow, there are different options of where to stay while you are in town. From castles to hotels and everything in between, find out below what will best suit your needs.
Castle Hotel & Spa
Looking to soak up the sunshine on beautiful castle grounds? The Castle Hotel & Spa mixes beauty with a hint of spook to make this the perfect place to stay in the fall during the Halloween season. This estate overlooks the historic Hudson River and has a health and fitness center, whirlpool, jogging paths, and an outdoor swimming pool. After an event-filled day in Sleepy Hollow, coming back to this gorgeous castle would be a dream come true.
Book now before their limited amount of rooms fill up before the Halloween season!!
Sleepy Hollow Hotel
The Sleepy Hollow Hotel is where business meets pleasure in the heart of American folklore. This stunning hotel has an indoor pool with a connected sauna, fitness center, and bar + lounge. Just minutes away from downtown Sleepy Hollow, grab some in-house Starbucks Coffee and head on over to your fun-filled day of Halloween events.
Other Hotels
There are a ton of other hotels in the Tarrytown area that may have what you are looking for. Whether you’re wanting something more affordable, simple, or just have points from your credit card that you want to use, there is definitely not a lack of hotels to stay at. 
Check here to see what is available for your stay.
Airbnb
Wanting something that feels more like home or wanting a more unique experience? Check out Airbnb’s website for availability during the weeks you’re wanting to visit. Airbnb’s are great for bigger parties. You don’t have to spend a fortune on multiple hotel rooms and you can become more immersed in the area.
Check out Airbnb’s website for more details and see what’s available near Sleepy Hollow.
How To Get Around Sleepy Hollow
From New York City, there are five main ways to get to Sleepy Hollow:
- Car
- Taxi
- Train
- Bus
- Subway
Want to stay in New York City, but still have an adventurous night, then check out the top 6 best things to do at night in NYC.
If you have your own car or rented a car, driving is going to be the fastest and cheapest (granted gas prices don’t go up another $4 a gallon). On the flip side, if you take a taxi, it may be quick but it is going to cost upwards of $200 one way.
Cheaper and more common ways are the Hudson train which takes approximately 50 minutes and costs between $9 to $21.
The subway is just a tad longer at one hour and 20 minutes, ringing in at about $10 to $23.
And finally, the bus is the longest route at about two and a half hours and only slightly cheaper than the rest at $8-$10.
Once you arrive in Sleepy Hollow or to where you are staying, getting around is quite easy on foot. If you want, you could easily use a car service like Uber or Lyft or utilize their public transportation to get to all the Halloween events you have planned. Luckily the town is pretty small so whichever way you plan to get around, you won’t be wasting time getting from one place to the next.
Want to stay in New York City this Fall season then don’t forget to check out my complete guide to New York City Here.
Last Thoughts
There’s no doubt that the story “The Legend of Sleepy Hollow” is the reason why the town has become such a popular Halloween destination. Whether you’re looking for the best Halloween events in Sleepy Hollow, NY or have been itching to visit, either way this is a destination and trip you won’t easily forget.
XOXO,
Anna
Anna is a traveler, blogger, and entrepreneur who can’t keep herself still. She’s always on the move, whether working hard on a new passion project or exploring a new city as a part-time digital nomad. Dare to keep up? Check out The Tatted Nomad for everything digital nomad, social media marketing, mental health, and travel (and to see her latest addition, Novah, her service dog and travel companion). As a psychotherapist (to be) she also offers insights about your mental health related questions – anything you see that isn’t covered but you have questions about? Let her know!
