I’ve checked Sleepy Hollow, NY off the spooky travel bucket list. Well, an initial visit anyway. Now I’m desperate to go back and experience Halloween there. But that’s another post for another day.
Working for a nonprofit doesn’t lend itself much to travel, but I have been lucky enough to visit New York three times now for my job. (That’s what happens when you’re the young single millennial in the department…a fate I am happy to accept if my boss happens to be reading this.)
The last time I visited New York was the spring of 2016. While I fly into New York City, I spend my time just north of the city in the Hudson River Valley. It wasn’t until I got home after that 2016 trip that I thought to look up how close Sleepy Hollow was to where I stay, though.
The answer? Ridiculously close. Like…10 minutes and less than five miles away.
So I decided the next time I was sent to New York, I’d spend an extra day or two bumming around Sleepy Hollow. That chance came earlier this month, and it was SO worth to trip.
Here’s my day in Sleepy Hollow:

It’s crazy to think this village was founded more than 100 years before America was even a country. I love how much history New England holds.
The interesting thing is up until recently (1996 recently), Sleepy Hollow was actually called North Tarrytown. In 1996, the village adopted its traditional name. Sleepy Hollow is only 5.1 square miles, 55% of which is water. Just over 10,000 people live there, and the village is located 30 miles north of New York City.

I started my day in Tarrytown at Coffee Labs Roasters, per my friend Matt’s recommendation.

Inside was the most perfect small town coffee shop you could imagine. My plain old latte was delicious, as was my cranberry scone. After sitting for a few minutes to enjoy breakfast, I set off on my walking tour of Tarrytown and Sleepy Hollow.

When I walked down Main Street a bit and could see the Hudson River in sight, I decided my first order of the day would be walking all the way to the waterfront for some photos.

I mean, how could you not want to capture that view? (You’ll have to forgive the Texas girl who lives in the land-o-flat and isn’t used to hills and views and such…)
The only thing I didn’t take into consideration? That New York has train tracks along the Hudson which I would have to find a way over.

As I walked on, I realized the street signs had changed. They were now black and orange and…what did I see at the top? A Headless Horseman?
Yup! I was officially in Sleepy Hollow. After wandering a few more blocks, I managed to make my way down to the water.

There I discovered Ichabod’s Landing! As I wandered, I was so charmed with these waterfront apartments. In reality, I was wandering past million dollar townhomes. Eek! They were gorgeous all the same. And they gave me these views…

A view of the Sleepy Hollow Lighthouse.

And the Tappan Zee bridge!

I had to snap this photo for my niece, who I knew would love seeing a firefighting boat.
After spotting how close I was to the Sleepy Hollow Lighthouse, I made it my new mission to get there. Unfortunately, I was totally blocked by construction via my current path and wasn’t brave enough to venture past the chain link fences. So I wandered in a different direction trying to get there.

Which led me to Barnhart Park and this charming park detail – an abstract Headless Horseman! I could tell I was back on the wrong side of the tracks to get to the lighthouse, so I gave up and wandered back into town.



According to Wikipedia, the village of Sleepy Hollow only has 27 police officers – this is the building they call home. How gorgeous is that stained glass? I love that they embrace “The Legend of Sleepy Hollow” in their city buildings.

They also embrace the story on their city vehicles! Some of the police cars I spotted were black and orange.

Others were blue, but every single one included a Headless Horseman emblem. (Even the street sanitation vehicle I passed several times but never managed to snap a photo of!)

Some of the local shops embrace the story as well, like the Sleepy Hollow Bicycle Center. This legitimately made me feel like I was walking through a spooky Stars Hollow.

Artwork on the windows at the…post office!

When I asked on social media and via my email newsletter for your Sleepy Hollow recommendations, the number one place everyone told me to eat was the Bridge View Tavern…so I did! I was there shortly after they opened, so it was pretty quiet. I enjoyed sitting at the bar, relaxing a bit with my Von Trapp beer and flatbread.
After lunch, it was time to meet up with the lovely Danielle of Verona Black (you must go check out her Etsy shop!) who served as my personal tour guide at…

…the Sleepy Hollow Cemetery! Danielle was a wealth of knowledge and knew exactly where to take me. (And I promise she was really there even though we never managed to get a photo together…)

The first thing Danielle pointed out to me? The Strange Family’s plot!

Her tour included going straight to Washington Irving’s grave. These headstones were so gorgeous, weathered over the years and all cut in different shapes. His is easy to spot in his family’s plot – it’s the only one with rounded edges. (That I remember, at least.)

We continued wandering towards the Old Dutch Church, which is the church that appears in “The Legend of Sleepy Hollow.” Its yard is technically not part of the Sleepy Hollow Cemetery, but the two are adjacent and you can walk from one to the other and back.

It was so cool seeing such old headstones. We just don’t have this kind of age on our historical sites here in the south.

Hangin’ out at the mausoleum with the ghouls…

Our last stop in the Sleepy Hollow Cemetery was the bridge. Now…this isn’t the original bridge from “The Legend of Sleepy Hollow.” That one never actually existed. But this one is a pretty good substitute, in my opinion. I love the thatched rails.

“Do you need Sleepy Hollow souvineirs?” Danielle asked me on our way to the cemetery.
“Um, OF COURSE!” I replied. So when we finished there, she brought me to Bella’s Boutique, one of the few spots in Sleepy Hollow, apparently, that has a few goodies for us spooky kids all year long. And Bella’s did NOT disappoint.

Books galore! I wanted to take them all home…my need to get home outweighed my need for books.

Coffee mugs and shot glasses for all!

Personally, I love collecting post cards from every place I visit, so I grabbed several as I wandered the store.

That soap is pumpkin-scented and even me, your resident no-pumpkin-anything friend, loved how it smelled. I’m also regretting not bringing home that black Sleepy Hollow T-shirt…

There was also art from a few locals. I loved this black and white piece.

I had a bit of a lack of space in my suitcase (I packed in my smallest one for a full week since I knew I’d be toting it all over NYC the following day.), so I bought as many flat souvenirs as I could!
Once we were done at Bella’s, Danielle took me back to my hotel. I wanted to go back out for dinner (I had my eye on a place called Ichabod’s), but I was SO worn out from my walking tour that I crashed.
There were a few more places I wanted to see, but I just didn’t get there without a car or because they weren’t open for the season just yet:
- Sunnyside, Washington Irving’s estate
- Lyndhurst Mansion, whose exterior was used for Dark Shadows
- Philipsburg Manor, which is the epicenter of spooky fun during Halloween season from what I’ve been told
I guess I have good reason to return…and soon! (Hopefully ,I get sent back to New York for work soon…)
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Have you visited Sleepy Hollow?
I’d love to hear what you recommend checking out, especially if you’ve visited at Halloween when there are SO many other activities to enjoy. (Read more about those here.)
Now then…to start planning that trip to Salem…
Happy haunting,

P.S. Thank you to Jim from visitsleepyhollow.org for kindly answering my travel questions I sent his way!



Laura McCartney
Wow!! Thanks for the tour, I must put this on my bucket list. Thank you so much for sharing with us
Miranda | Spooky Little Halloween
Definitely worth a visit!
Candace Jedrowicz
How wonderful! I want to live in a spooky Stars Hollow!
Miranda | Spooky Little Halloween
Me too! I’m really afraid if I visit Salem I won’t come home for that exact reason…
Spooky Sarah
It looks like such a fun trip and you took some fantastic photos! I visited there on a hot August day about 5 years ago, taking the train up from NYC. I’ve been itching to go back and explore more since I didn’t get as much time as I wanted in the cemetery. I bet it is so stunning in the fall!
Miranda | Spooky Little Halloween
Sounds like it’s time for a Samhain Society field trip! ;)
Chelsea Celaya
I’m not too interested in New York, but Sleepy Hollow would definitely be a place I’d want to wander in. It looked like such fun! Hope you get to go back soon!
Miranda | Spooky Little Halloween
It’s a very cool little town. I’d definitely go back during October to see it in all its glory.