best things to do in sleepy hollow new york

9 Best Things to Do in Sleepy Hollow New York

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Are you ready for the best things to do in Sleepy Hollow New York? You should feel excited and ready to go on this Hudson Valley adventure, because we’re at the height of Spooky Season – which is my favorite time of the year!

I mean, what’s not to love? Pumpkins all over the place, changing leaves, ghost stories, cool crisp air, maple-flavored coffee, apple picking. I love everything about October. Everything. 

Usually, the weather is very comfortable in this part of the northeast, too. All you need to wear is a light jacket and a stylish pair of jeans. 

Anyway, Sleepy Hollow is the perfect destination for a quick autumn or Halloween getaway. You’re probably already familiar with this famous village, too.

After all, The Legend of the Headless Horseman seeps into all aspects of life in this scenic part of New York State. 


things to do in sleepy hollow new york: read the original legend

Why You Should Visit Sleepy Hollow

As you know, I write a lot about loving New York City. I live relatively close to New York, so it’s easy for me to take several day trips to the Big Apple. I learn something new every time I visit. Not to mention, I’m even a huge advocate for solo travel in New York and truly believe it’s a great destination for a plethora of reasons.

However, escaping the city for a day or two is always a wonderful idea. Both for a change of scenery and breathing room from the crowds at Times Square and Rockefeller Center. And, you guys, New York State is absolutely beautiful especially in the autumn months. 

And luckily for you, it’s very easy to reach Sleepy Hollow from New York City. All you need to do is take the Metro North train from Grand Central Station. Boom! Easy.

This particular train ride is (more or less) direct and only takes about an hour to reach Philipse Manor station, which is the stop for Sleepy Hollow. Honestly, you could even do Sleepy Hollow as a day trip and base yourself in Manhattan. 

things to do in sleepy hollow ny include buying fall decorations

However, although I adored Sleepy Hollow and think it’s the perfect fall day trip from New York, you might experience two major drawbacks if you’re not careful about planning in advance.

  1. You need to have a car in Sleepy Hollow. With the exception of Metro North, Westchester County isn’t very public transportation friendly at all. Luckily, overflow parking is available at the main visitor’s center near the Old Dutch Church, and with the exception of the Great Jack O’Lantern Blaze, Sleepy Hollow’s attractions are within walking distance of each other. Uber also frequently operates in the area.  
  2. Ticket reservations are crucial. Sleepy Hollow is understandably popular at Halloween. However, even though the events seem endless, many venues are small and tickets are very limited. So, buy your tickets as soon as they are on sale on the Historic Hudson Valley website. You’ll thank me later. 

Do your research ahead of time, and you likely won’t have many problems.

things to do in sleepy hollow include many pumpkins 

Things to Do in Sleepy Hollow New York

Just a word of warning. I visited Sleepy Hollow in October – which is obviously the best time to visit this Hudson Valley village.

However, I believe that some of these attractions are only available during the Halloween season. If you’re coming in September and November, double check what’s available so you don’t leave Sleepy Hollow feeling bewildered and disappointed. 

Without further ado, here are the best things to do in Sleepy Hollow New York!

places to stay in sleepy hollow ny don't include the cemetery
The 1st of things to do in Sleepy Hollow New York: a cemetery!

1. Tour Sleepy Hollow Cemetery 

First, you want to visit Sleepy Hollow Cemetery. I consider this cemetery a “must see” for both horror and history buffs. 

Believe it or not, this cemetery is about 90 acres in size, so it’s a bit unlikely that you’ll see the entire area on a single trip. I was actually surprised when I first arrived and realized just how massive this cemetery is. Nor did I have enough time to see all the graves. 

Not to mention, Sleepy Hollow Cemetery is the final resting place of several rich and famous people, such as Andrew Carnegie, Elizabeth Arden, and William Avery Rockefeller. Don’t miss out on some of the beautifully constructed mausoleums. 

sleepy hollow travel guide - don't miss the cemetery
Sleepy Hollow Cemetery: Among the Top Things to Do in Sleepy Hollow New York

At the cemetery, it’s advantageous to book a guided tour. There are several options and times to choose from, especially in October.

If you’re interested in history, go with a two hour day tour that takes you to the most famous graves. This tour is available in the day or in the evening with lanterns. For those of you seeking something spookier, then go with the haunting “adult only” Murder and Mayhem tour at night.  

Interesting fact: Washington Irving requested that the cemetery change its name from Tarrytown Cemetery to Sleepy Hollow Cemetery. This request was honored after Irving’s death. 

sleepy hollow in october you'll have crisp cool weather
Can You Find Washington Irving’s Grave?

2. See Washington Irving’s Grave

Of course, you can’t come to Sleepy Hollow without seeing Washington Irving’s grave. 

His actual grave is blocked off from the public. According to my tour guide, visitors were taking bits and pieces of his grave, so the cemetery took steps to protect it. Which, yeah, don’t take bits of tombstones as souvenirs. It’s not cool.

The area around Irving’s grave is decorated for Halloween. A small Jack O’Lantern, one with a mischievous and wicked grin, is left near Irving’s grave, and is jokingly said to be a gift from the Headless Horseman. 

go to the old dutch church when seeing sleepy hollow in october

3. Experience History at the Old Dutch Church

The Old Dutch Church is a major landmark in Sleepy Hollow. You’ve probably heard of it if you’ve read Irving’s classic story. Ichabod Crane just needs to reach the holy building to escape the clutches of the Horseman. A bridge, located right near the Old Dutch Church, is a structure that Headless Horseman supposedly cannot cross.

Honestly, the bridge isn’t anything special at all, but the Old Dutch Church is worth visiting. 

The church was completed in 1697, which is incredibly old for US standards, and has been in service all those years, with the exception of the Revolutionary War. The Church is still active and holds special services throughout the summer and on big holidays such as Christmas Eve. 

There is no parking on site for the Old Dutch Church. Park in the cemetery or at the nearby visitor’s center overflow lot. 

Read More: 15 Best Day Trips from NYC in the Fall

things to do in sleepy hollow: listen to a master storyteller

4. Listen to a Master Storyteller’s Spooky Legends

Want to hear a true storyteller regale you with Irving’s spooky and eerie words? Then you need to make time for a performance of “Irving’s Legend.”

This re-telling features all the characters you know and love such as Ichabod Crane and the Headless Horseman. Even if you’ve read the story a billion times, hearing a storyteller makes the setting come alive and stirs your emotions. Honestly, this event was one of my favorites in all of Sleepy Hollow. I highly recommend it to all visitors. 

Mind your manners at the performance. No photography is permitted (my photo wasn’t taken during the performance) when the storyteller is on stage and ready to go. Also silence your phones. 

Last but not least, buy tickets in advance especially if you want an evening performance. They sell out rather fast. 

Read Irving’s Words: The Legend of Sleepy Hollow & Other Tales

things to do in sleepy hollow ny: stop in nearby tarrytown

5. Shop and Eat in Adorable Tarrytown

As much as I liked Sleepy Hollow, I personally don’t think it’s as great of a place to eat and shop as nearby Tarrytown, which has several more options available for tourists. 

You’ll encounter a wonderful Greek restaurant (Lefteris Gyro), a delightful coffee shop (Coffee Lab Roaster Inc), a Burger Bar (Little B’s Burger Bar), a bakery (Tarrytown Pastry Chef), and so much more! Take a stroll and see what places tickle your fancy. You won’t go hungry in Tarrytown. 

Not to mention, Tarrytown has a very cool 1920s vibe, and makes for some excellent photographs. Stop and take pictures! 

Walking between Sleepy Hollow and Tarrytown isn’t a problem. Parking is limited, and it’s understandable if you don’t want to move your car around throughout the day. 

On a Road Trip? Check Out Lonely Planet’s Best Mid-Atlantic Trips

sleepy hollow travel guide: see the unsilent picture

6. Watch a Creepy Unsilent Movie

Need more of the best things to do in Sleepy Hollow New York? Then go to the Unsilent Picture for something new and cool and different!

Unlike other events, this film is based off a completely different Irving short story called “The Adventure of the Mysterious Picture.” It was cool watching the movie, because I had never read this specific tale, and had no idea what would happen next. 

As the silent movie plays, an actor uses a variety of tools to add all the sound effects. His timing is impeccable! 

Without a doubt, the Unsilent Picture is another one of the spooky things to do in Sleepy Hollow New York. I’m still thinking of the doctor’s madness long after my trip has come to an end. I want to read the original story now, and see how it compares to the film experience. 

Read All of Washington Irving’s Works

the blaze is one of the best sleepy hollow ny things to do

7. Take a Drive to the Great Jack O’Lantern Blaze 

Okay, so, the Great Jack O’Lantern Blaze isn’t technically in Sleepy Hollow. You’ll have to drive twenty minutes to nearby Croton-on-Hudson.

However, don’t let the distance stop you. Trust me, it’d be a huge, huge shame to miss this glorious pumpkin light spectacular. 

At the Blaze, you’ll walk through a magical park of 7,000 illuminated pumpkins. I felt like I was dropped into The Nightmare Before Christmas. 

You’ll discover a Pumpkin Museum of Art, a windmill, two stunning bridges, and a huge Statue of Liberty among the jack o’lantern attractions.

things to do in sleepy hollow new york: spiders and pumpkins
Need things to do in Sleepy Hollow New York? Without a doubt, the Great Jack O’Lantern Blaze!

You need to buy tickets to the Great Jack O’Lantern Blaze well in advance. I’m not kidding.

As an event constantly promoted on Time Out New York, it’s not surprising that all the best time slots sell out fast. I’ll give you an example. I purchase my 9:30 entrance ticket on September 3rd for the Blaze on October 5th. All previous time slots? Already gone. You need to act fast. 

But the hassle is so, so, so worth it.

sleepy hollow in october has lots of decorations
Not sure what to do in Sleepy Hollow? Take pumpkin seflies!

8. Feel Bloody Terrified at Horseman’s Hollow

Do you want a good scare? Then purchase tickets to Horseman’s Hollow. Sadly, I didn’t have a chance to go to Horseman’s Hollow, but I’ve heard incredible things from people and I hope to go next year!

Check out this preview for Horseman’s Hollow. Just this video alone has me feeling a little terrified! 

Like all attractions, buy tickets in advance, because the best slots sell out right away. It’s also recommended not to bring small children to Horseman’s Hollow for obvious reasons. 

Scary, right? Go at your own risk, my friends, haha. And scream as loudly as you want. No one is judging you.

Read More: “Ghostland: An American History in Haunted Places”

things to do in sleepy hollow new york include seeing a Rockefeller estate

9. Pretend to be Rich at Kykuit Estate 

Last but not least, you don’t want to miss the Rockefeller family’s stunning Kykuit Estate. Kykuit is one of many gorgeous mansions and estates that you’re permitted to tour in the Historic Hudson Valley. 

For the Kykuit Estate, you have several ticket options available to you. I personally chose the Classic Tour due to its price and time. The Grand Tour covers a lot more, including some upstairs room, but a ticket was a lot more expensive, and when tours are longer than two hours, my eyes start glazing over, haha. 

The grounds of Kykuit are absolutely beautiful. The estate is on top of the highest point in the nearby area. So the views are spectacular especially when the leaves are changing colors. 

Without a doubt, Kykuit Estate is one of the best things to do in Sleepy Hollow New York. 

exploring the cemetery is what to do in sleepy hollow

Places to Stay in Sleepy Hollow NY

Unfortunately, you don’t have too many hotel options right in the heart of Sleepy Hollow. Believe it or not, I don’t think there are any hotels in Sleepy Hollow itself.

Are you surprised? I was at first too, but after visiting Sleepy Hollow, the lack of hotels makes a lot of sense.

Sleepy Hollow is small. Not to mention, it’s a surprisingly packed town and sometimes feels more like a small city than a quaint riverside village. A lot of the homes have actually been converted into apartments to accommodate the local population. 

what to do in sleepy hollow ny? carve emoji pumpkins

Budget accommodation, especially in the fall months, is also surprisingly difficult to find in this part of the Hudson Valley.

You’ll have much better luck finding hotels in the hills of Tarrytown, especially along major roads such as Route 119. 

I stayed at the Sheraton Tarrytown Hotel on Route 119. This midrange hotel suited my needs. It was clean and quiet, and only a five minute or so drive to Sleepy Hollow’s main attractions. There was also plenty of free parking available for hotel guests. The staff was very kind and welcoming, too. 

gardens are among the things to do in sleepy hollow

If you’ve money to splurge, however, I’ve heard amazing things about Castle Hotel & Spa in Tarrytown. This small luxury hotel is perched upon one of the highest points in the lower Hudson Valley. It legitimately looks like a castle you’d see in Scotland or Ireland.

So, if you’ve money to burn and want to be pampered like a Queen, then I recommend checking out this hotel. Don’t go into debt over it, though. 

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what to do in sleepy hollow ny: carving pumpkins everywhere
The Best Things to Do in Sleepy Hollow New York: Carving Pumpkins!

I hope you enjoyed reading all about the best things to do in Sleepy Hollow New York. Have you ever gone to Hudson Valley? What were your favorite places? Or just share a scary story in the comments! 

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