Spend a day in the heart of Sleepy Hollow and Tarrytown, where history and legend intertwine with charm and mystery.
Horseman bagels
You’ll need some fuel for your day exploring Sleepy Hollow and Tarrytown, and we highly recommend starting with a classic New York bagel here! Not only are they delicious, but this spot is perfectly situated right at the beginning of Sleepy Hollow’s Main Street.
See MoreSleepy Hollow Bookshop
We love exploring local bookstores, and this spot is a gem with its fun Halloween-themed books! It also features a cozy café where you can grab a book and unwind. It’s the perfect family-friendly spot to relax and stay in theme for a spooky day in Sleepy Hollow.
See MoreScenic Hudson RiverWalk Park at Tarrytown
After you’re done shopping and soaking in the Halloween décor around town, head to the end of the street where you’ll find a beautiful walking path along the Hudson River. You’ll get stunning views of the Cuomo Bridge, and at the end of the path, you can also catch a glimpse of the famous lighthouse!
See MoreWelcome to Historic Sleepy Hollow Sign
On the walk to our next stop this is a great “instagramable” spot to commemorate your sleepy hollow day!
See MoreHorsefeathers
After all that walking and soaking in the views, we definitely worked up an appetite! We’ve made this Halloween day trip an annual tradition, and this spot is a must. Not only is the food incredible, but the Halloween décor is our favorite! It feels like you’re stepping into an “I Spy” book, with every detail carefully placed around the restaurant, so be sure to take it all in!
See MorePhilipsburg Manor
If you are a fan of the headless horseman story you must check out some iconic landmarks such as this one!
See MoreHeadless Horseman Bridge
Just across the street from Phillipsburg manner you can see the famous bridge from the spooky tale of the headless horseman! A must see if you are a fan of the story.
See MoreSleepy Hollow Cemetery
Just a short walk from the bridge, you can visit the gravesite of author Washington Irving. Even if you’re not a fan, it’s a lovely historical stroll, and the gravestones offer a glimpse into the town’s rich history!
See MoreCoffee Labs Roasters Inc.
A sleepy hollow day wouldn’t be complete if you don’t visit its neighboring town- Tarrytown! We love this cafe especially during October because they specially make Halloween latte art! Plus it’s a dog friendly spot so expect some furry friends while enjoying your coffee.
See MoreTransom Bookshop
There are so many cute shops to explore in town but we reccomend this book store because it has a special section of Sleepy Hollow/ headless horseman section that is a great memento from your day!
See MoreTrilogy Consignment
If you’re on the lookout for eclectic décor, clothing, or unique trinkets, this is a fantastic place to shop! We bought a horror tarot deck and Halloween sweatshirt here that we can’t wait to use!
See MoreWashington Irving's Sunnyside
Since this is a spooky day inspired by sleepy hollow it is a must to visit the estate of the author! This estate is beautiful and a must on your trip!
See More