What to Do in Sleepy Hollow for Halloween | Upstate NY

What to Do in Sleepy Hollow for Halloween | Upstate NY

Sleepy Hollow has been on my list for a while as an October activity. I love Halloween so visiting the stomping grounds of the infamous Headless Horseman seemed intriguing.

It’s amazing to me that Sleepy Hollow is actually a real place. The Legend of Sleepy Hollow is one of my favorite Halloween stories, so it was really cool to be able to visit where the story was set. It’s odd too because I live close enough to it that I feel like I should’ve heard about being able to visit there long ago. At least I know now.

For those of you who aren’t familiar with this town, Sleepy Hollow is where the ghost of a Hessian soldier, the Headless Horseman, awakens each night in search for his head. He’s been searching for a pretty long time since it was originally lost to a cannonball during the American Revolution. It’s a historical and Halloween-centric tale! Sort of…



The village of Sleepy Hollow sits on the scenic and rolling Hudson River Valley in Tarrytown, NY. Historically, the area was founded by Dutch settlers, which is where the ‘old country’ folklore originates from. In modern times, the town still adorably celebrates its roots and the famous Sleepy Hollow legend by going all out for Halloween.


What to Do in Sleepy Hollow for Halloween

Three friends and I arrived late in the morning for an early lunch and to walk around. The first thing we noticed was how all the street signs were orange. How fun! They’re like that all year round.



Even the firetrucks were in theme. I wonder what the people who live here think of that.



The main area of the town was quaint. Parts of the street were closed off so that we could walk freely around. The first thing we did after parking (which was a bit hard to find), was to eat at a restaurant that overlooked the Hudson River from a hill. This was nice and I recommend doing that in the earlier part of the day. Once we were full, we were off to start our activities.


Sleepy Hollow Itinerary

My friend Ashley, whose a master at the itinerary, planned everything. You can read her coverage of our spooky adventure at her blog. We covered at lot of ground in one Saturday, so if you have to do Sleepy Hollow in one day like we did, definitely follow this itinerary.

  • Drive up to Sleepy Hollow in the morning
  • Lunch/farmers market/walk around in Sleepy Hollow
  • Tour Lyndhurst mansion 3pm
  • Dinner/walk around Sleepy Hollow
  • Cemetery lantern tour 7pm
  • Horseman’s Hollow haunted trail 9pm
  • The Great Jack O’ Lantern Blaze 10:30pm
  • Head back to NYC around midnight or so

Book things as early as you can because Sleepy Hollow gets packed in October and you don’t want to miss out!


Lyndhurst Mansion

The Lyndhurst Mansion is in Tarrytown and overlooks the Hudson River. It’s the old Gothic Revival mansion of the “robber baron”, Jay Gould. Originally built in 1838, it expanded in opulence throughout the rest of the 19th century.


We found a wishing well and Ash wanted to see how deep it went, so she dropped a rock. It went about a foot! #Fail


The grounds are about 67 acres and are pretty to walk around. When we went, they had decorated the grounds and interior with Halloween decorations. That was fun, but I also want to see it as it normally looks one day.




As usual with these old mansions, the architecture was amazing so it’s definitely worth a visit. It looks its best when there is enough sun to shine through the big windows and verandas.


Me doing cartwheels in the backyard of the mansion


Ashley being quizzed on the tour


The Master bedroom


The Master bedroom overlooks this library


Cemetery Lantern Tour

The Cemetery Lantern Tour in Sleepy Hollow was my favorite event of the day. It was pretty unique. Sleepy Hollow cemetery is odd and hauntingly beautiful. The unduating hills and ornate graves and mausoleums created a fantastically Halloween-esque atmosphere.



Sleepy Hollow is a very historic town, even outside of it’s spooky horseman legend. The wealthy NYC elite of the 19th century had built many mansions throughout this region. This is why relatives of these renown families have their “graves” here. The Vanderbilt grave is one very ostentatious plot in particular. It was truly overwhelming in size and we could feel the wealth that they had still emanating from it.

Our tour guide told us stories of how these families had started building their mausoleums prior to death and would compete to make their resting place larger than the other. Nuts.



My favorite grave (weird to say) was Andrew Carnegie’s. He was a wealthy man of industry as well, but his grave was something you could easily walk past. It was minimalistic and small. I think that says a lot about him as a person.

There’s a bunch of tours to choose from when booking the Cemetery Lantern Tour. We did the one at night so that it would be foggy and creepy. The best part of this tour is that the only light they give you to maneuver in the dark with are lanterns!



So imagine how cool that is; carrying a lantern at night in the fog, and visiting the actual grave of the Headless Horseman!


Horseman’s Hollow Haunted Trail

This was the best haunted house I’ve ever been to and I’m not just saying that. First of all, they have entertainment and food as you wait on line. That right there gives them brownie points. Luckily, we didn’t have to wait in line because Ashley was awesome and had bought the fast passes a while back.

The Haunted House here wasn’t just a house either. The Phillipsburg Manor, where it’s hosted, is fairly large and had transformed the entire grounds and all of the buildings into a haunted landscape and playground.


From the Pumpkin Blaze


There were some creepy surprises that happened along the way and I don’t want to give them away. All I know is that it was hysterical to watch. I don’t get scared, I get startled. This is why I can revel in watching the people who actually get really scared squirm.


The Great Jack O’Lantern Blaze

The 18th century Van Cortlandt Manor is the epic home of the Great Jack O’Lantern Blaze. This was the last activity of the day and it was the perfect one to end the night with.



When we arrived at the Manor we entered through a giant pumpkin archway. This was the beginning of the trail of 7,000 hand-carved, illuminated pumpkins. A lot of these were real pumpkins so it was very impressive.



We were surrounded by pumpkins on all sides. They were in all different shapes and configurations: the Pumpkin Zee Bridge, famous cartoons, a pumpkin planetarium…


Pumpkin Zee Bridge aka the Tappan Zee Bridge in NYC


The Pumpkin Planetarium


Having gone to the RISE of the Jack O’Lanterns in Old Westbury Gardens on Long Island, I was already a fan of these pumpkin fanfares. However, this was definitely the biggest one that I’ve been to.


The Legend of Sleepy Hollow

For those of you who don’t know, the Legend of Sleepy Hollow is actually a short story written by Washington Irving. It follows the hapless school teacher, Ichabod Crane, in the 1700s. He moves to the town of Sleepy Hollow, NY and gets embroiled in its haunted curse.
Ichabod is in love with Katrina Van Tassel and on his way home, after a failed attempt at wooing her, he finds himself on an eery, dark, and supernatural path in the forest. That’s when he runs into the terrifying Headless Horseman riding a decrepit horse. This ghostly rider has no shoulders and holds his head in his saddle.
“In a frenzied race to the bridge adjacent to the Old Dutch Burying Ground, where the Hessian is said to “vanish, according to rule, in a flash of fire and brimstone” upon crossing it, Ichabod rides for his life.”
For what happens after that, you’ll have to read the story or watch the movie. Can’t spoil it for you.

Was the Legend of Sleepy Hollow True?

Yes! But not the supernatural part. Near the end of the Revolutionary War, the area was full of reckless Hessian Jagers (German mercenaries contracted by the British). A real headless corpse of a Hessian soldier was found in the area and buried in an unmarked grave in the Old Dutch Burying Ground. We visited this grave!


Washington Irving's grave Sleepy HollowWashington Irving’s grave from the Cemetry Lantern tour


Ichabod Crane was also real! The actual person was a military man who had served in the War of 1812. Washington Irving had met him at Fort Pike in Sackett’s Harbor one night in 1814.

How to Get to Sleepy Hollow

Sleepy Hollow is only about 30 miles from Manhattan. It’s super easy to get to by car and you can visit the town in one day. You an also easily reach it by using the Metro North trains from Grand Central. When you get there by train, you’ll see the town has set up signs with maps of where all the main attractions are for October.


Dancer jumps at Lyndhurst mansion


I also thought it was funny that when we were in Sleepy Hollow there was a sign to the town of Pleasantville. If you’ve seen that movie then you’ll think it’s cool that this famous movie town has the directions to another famous movie town too.



Are you brave enough to visit the eerily enchanted Sleepy Hollow?