One of my favorite things to do in the fall, and especially around Halloween is take a day trip to Sleepy Hollow from NYC. This town is picture-perfect with orange street signs, small pubs, and the cutest Halloween decor. At night it becomes ominous and spooky. Here are the best things to do in Sleepy Hollow!
THE STORY OF SLEEPY HOLLOW
Apparently there are a few different versions of this story. The one I was told while visiting was different than the movie version with Johnny Depp. Here is the story I was told…
A soldier fighting in the American Revolution was decapitated by a cannonball during battle, he later got the name “the headless horseman”. Now, each night he rides to the scene of the battle in search of his head. One night, a man named Ichabod Crane comes across the headless horseman as he solemnly rides home after being denied the hand of Katrina Van Tassel, the daughter of a wealthy farmer. (Crane was defs a gold digger) Crane is shocked when he notices the mans head is missing and flees, but is unable to escape. There are many theories about what happened to Crane that night, but you can read the full legend of Sleepy Hollow here.
The best things to do in Sleepy Hollow, NY.
GETTING TO SLEEPY HOLLOW FROM NYC
Take the north metro Hudson line from Grand Central to Tarrytown. We paid $22 each for a round trip ticket. Sit on the right side of the train for the best view of the changing colors during fall. Once you get off the train it’s a quick 10 minute walk to the Main Street of Sleepy Hollow.
WHAT TO DO IN SLEEPY HOLLOW
Note: Many of the activities that normally happen this time of year in Sleepy Hollow have been cancelled due to the ongoing pandemic. Though I did update this guide to the best of my knowledge, be sure to check before you go. Regardless, I think a day trip to Sleepy Hollow makes for a great fall day!
Also, reservations are required for all activities so be sure to make them in advance!
Westchester Craft Crawl & Irvington Farmers Market
If you love art, you’ll want to stop by the Westchester craft crawl held on October 24-25. There are a few towns located on the crawl route and Tarrytown is one of them. You’ll find all different sorts of art from clay, wood, fiber, metal, jewelry and mixed media.
Before you reach Tarrytown there is the town is Irvington which has farmers markets on Saturdays. You’ll find different types of food, drinks and beautiful crafts to purchase.
Sleepy Hollow Cemetery
Next, explore the Sleepy Hollow cemetery where infamous people like Elizabeth Arden, Andrew Carnegie, Washington Irving and many more are buried. We grabbed a beer at the beer garden, took a picture with the headless horseman and strolled through the cemetery. We originally were going to walk around on our own but an older gentleman who volunteers around town gave us a small tour! The staff was also very helpful in answering any questions.
Sleepy Hollow Cemetery Tours
You can explore the cemetery on your own or sign up for a day or night guided tour. The night tour is extra spooky because the path is lit only by lantern. Check the site for reservations!
Tarrytown is the village right next to Sleepy Hollow and it’s an easy walk from one to the other! After the Cemetery, we walked around town a bit, looked at decorations and felt the spooky vibes.
Home of the Legend Tours
The description of this tour on the Sleepy Hollow site is “Take a spooky tour on the grounds of Washington Irving’s estate and go on a literature-themed scavenger hunt. A special exhibit highlights how the Legend has lived in the imagination of popular culture through the centuries since its publication.”
Don’t forget to reserve ahead of time!
Dinner at Horsefeathers
For dinner we decided to go to a cute spot called Horsefeathers. Most restaurants had a wait due to the time of year and this place was no exception. They had an outdoor bar set up so you could have a drink while you waited, which is always a plus! Since it was only the two of us we got in pretty quickly!
Inside the restaurant you’ll find Halloween and fall decor which made for a very cozy atmosphere. If you aren’t sure what to order, I got the Knickerbocker burger and Robert got the Broadway Dip wedge and both were great! Oh and the martinis were yummy as well!
Drinks at J.P Doyles
Obviously I have to add in a spot for drinks! On our way to the train, we walked back down Beekman street to grab a quick drink at J.P Doyles Restaurant and Public House. We were told that this place had great food as well, but it was a perfect little spot to finish the night!
The Great Jack O’Lantern Blaze
This event takes place in Van Cortlandt Manor which is only a few stops away from Sleep Hollow! Over 7,000 hand carved pumpkins light up the night at this halloween event. See the 25 ft tall jack o’lantern Statue of Liberty, step inside the pumpkin planetarium and so much more!
Hopefully next year the rest of the Halloween attractions will be back in Sleepy Hollow! But for now, make the most of this season with a day trip and enjoy what they do have!
Did you enjoy this post on the best things to do in Sleepy Hollow? Pin it for later!