A couple and their chihuahua dressed up as Jack Skellington and Sally from The Nightmare Before Christmas

Sleepy Hollow, NY: Lose Your Head On This Spooktacular NYC Day Trip

Okay, okay – clearly I’ve been hanging around my dad too much with that “hilariously” punny title 😉

Anyway, Happy Halloween! It’s my favorite holiday of the year, and fall is undoubtedly one of my favorite seasons.

A couple under fall foliage in Washington, DC
Kyle and I on a spectacular weekend in Washington DC in November a couple of years ago. Look at those leaves!

I love the smell of the leaves, changing colors before our very eyes from lush green to amber, burnt orange, and rich reds. I love the clothes – I can finally wear leggings, boots, plaids, and jean jackets without sweating on the subway or needing to layer my jacket with another jacket.  I love making my own homemade treats and baked goods, filling the house with the scent of applesauce and fresh whipped cream, homemade pumpkin spice creamer, and my Aunt Rose’s  chocolate chip pumpkin bread. And of course, as every good fan of scary movies, Tim Burton, and festive spooky decor, I love nothing more than Halloween – I think I get just as excited as the kids for all of the costumes, candy, and all of the Halloween TV/Movie specials.

This year, my boyfriend and I decided to take our dedication to the couples costume to the next level, going as Jack Skellington and Sally from The Nightmare Before Christmas.

A couple and their chihuahua dressed up as Jack Skellington and Sally from The Nightmare Before Christmas
Photo Credit: @madhattersnyc

What do you think? Did we pull it off?

For comparison, here is the picture from our first Halloween together, when we went as Charlie Brown and Lucy. Which do you prefer?

A couple dressed as Charlie Brown (holding a Snoopy dog) and Lucy (holding a football) from the Peanuts Gang

Besides dressing up and going out in the city that never sleeps (and especially so on Halloween), New York provides a plethora of wonderful fall activities throughout the season, in part thanks to the myriad of quaint towns dotting the Hudson River just a few miles up north.

Recently, I took a day trip to the most Halloween of Halloween Towns – Sleepy Hollow, New York! Many of you are probably familiar with Washington Irving’s famous short story, The Legend of Sleepy Hollow, in which a headless horseman terrorizes the small village of Sleepy Hollow. Sleepy Hollow itself seems all-too-aware of the legend, embracing it and capitalizing on it to become one of the most charming tourist destinations of the season!

How to Get to Sleepy Hollow from NYC

Sleepy Hollow is a quick train ride away from NYC. Take the Metro North local train in the direction of Croton-on-Hudson and get off at Philpse Manor.

That’s it! And it only costs $20 round trip, with trains leaving every hour on the 20.

Of course, if you really want to make a day of it, you could take the express train to Tarrytown, one stop before Sleepy Hollow. Tarrytown (the town that the Draper family lived in – Mad Men, anyone?) is an incredibly cute, quaint, picturesque town reminiscent of Stars Hollow (Gilmore Girls, anyone? Okay, I’ll stop with all the TV references). The old-timey main street in the city is lined with mom-and-pop shops, craft coffee houses, cute brunch places, and great pubs and restaurants. I’d recommend making Tarrytown your destination for food and coffee either before or after your visit to Sleepy Hollow – which is only 15 minutes away on foot. The entire town is totally walkable, by the way – no need to rent a car, unless you plan on making multiple stops along the way.

What to Do in Sleepy Hollow

Check Out the Tricked Out Houses

(Last pun, I swear!)

A house in Sleepy Hollow decorated for Halloween, with a ghost hanging form the window and a skeleton horse mounted by a "horseman" with a pumpkin for a head.
The Headless Horseman rises again, putting on his jack-o-lantern head to terrorize the town of Sleepy Hollow once more!

On your walk to/from Tarrytown, you can take in the sights of a town that takes its Halloween namesake seriously! Some of the most magnificent colonial-style houses put on incredible displays that felt like they came straight from the set of a Halloween movie.

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Part of me wished I was a kid again so I could go trick-or-treating in Sleepy Hollow – I bet nearly ALL of the houses give out full-size candy bars. No “fun” size treats here!

Visit the Old Dutch Church

Sign outside of the Old Dutch Church that says "The Old Dutch Church of Sleepy Hollow Buil 1687 by Frederick Philipse First Lord of the Manor in Use Since Except in Revolution
“In Use Except in Revolution” – i.e. this church predates the Revolutionary War and is STILL in use!

Founded in 1697, the Old Dutch church is a simple wooden structure much in the plain aesthetics of the Dutch Protestants. While the original structure remains, the interior was completely renovated in the original style, to look just as it did when it was first constructed.

Pop in and take a look at the incredible organ and brass chandelier, one of the few signs of “opulence,” and admire the incredible pumpkin carving skills of those in charge of keeping the church. Yup, that’s right – even the church in Sleepy Hollow gets decked out for Halloween.

Interior of the Old Dutch Church in Sleepy Hollow, NY with Chandelier, Pulpit, Organ, and carved pumpkins for HalloweenInterior of Old Dutch Church in Sleepy Hollow, NY with pulpit, chandelier, organ, and carved pumpkins for Halloween

Take a Tour of Sleepy Hollow Cemetery

One of America’s oldest cemeteries, Sleepy Hollow Cemetery is located directly behind the Old Dutch Church.


The oldest tombstone (that we could decipher) was from the 1730s…predating the Revolutionary War! Beware, though, lest you see some spooky guests haunting the hollow grounds…

Headless Horseman stands over Sleepy Hollow Cemetery visitor with a sword

Cross the Sleepy Hollow Bridge

Sign spanning a Bridge in Sleepy Hollow NY that reads "The Headless Horseman Bridge described by Irving in the Legend of Sleepy Hollow formerly spanned this stream at this spot

Visit Philipsburg Manor by Day…

For a true step back in time, return to the Colonial Era with a historical visit of Philpsburg Manor, a milling and trading complex that was once home to the Philpse family. The Philipse family was involved in the Atlantic slave trade, and as such owned 23 slaves who are largely responsible for constructing the buildings on the property. A house museum with artifacts from the time (and, rumor has it, people dressed up as colonialists in traditional clothing), Philipsburg Manor could be a much closer option for those New Yorkers wishing to get the Colonial Williamsburg experience.

…and the Horseman’s Hollow by Night!

By night, the wooded path winding towards Philpsburg Manor transforms into the Horsemans Hollow during the month of October! A sort of haunted trail designed for those age 10 and up, the hollow is home to many witches, goblins, and disturbed spirits…so enter if you dare! (Pro tip: Purchase tickets at least a couple of weeks in advance, and try to choose an earlier time slot if possible – wait times were up to an HOUR for those with later timed tickets!).

Decorations in Sleepy Hollow with Corn Stalks and Jack-o-Lantern head

Grab a Pint at J.P. Doyle’s

This fun pub with a spacious bar and an ample beer and food list is in the heart of the old town of Sleepy Hollow. Decked out with Halloween decor, it certainly sets the mood (or warms your hands) for a day out exploring the spooky streets…

Make it a Day and Check out The Blaze at Croton-on-Hudson

This spectacular display of thousands of carved pumpkins, pumpkin sculptures, pumpkin bridges, jack-o-lantern lights and jack-o-lantern displays is on my Halloween To-Do List for next year! I went to a toned down version of this event on Governor’s Island last year, but the one in Croton-on-Hudson is incomparable. An incredible spectacle to behold, the Great Jack-o-Lantern Blaze is located at the end of the Metro North Hudson Line, about 30 minutes past Sleepy Hollow.

Have you been to Sleepy Hollow or the Great Jack-o-Lantern Blaze? What did you think? Did you nearly lose your head to the Headless Horseman?! I’d love to hear from you, let me know in the comments!

Happy Halloween, everyone!



    1. girlingothamcity

      Thanks so much, Suzanne! You are always too sweet! We had a wonderful time in Sleepy Hollow/Tarrytown…it was a great change of pace and SO close to the city! I have a feeling I’ll be back soon when I need to escape from the city, esp. now that I know how easy it is to get there.


  1. Mad Hatters NYC

    You know I’m here for alllllll the puns 😉

    We’ve been to The Blaze and it’s incredibly fun, but we keep missing the boat with Horseman’s Hollow. Maybe I’m afraid it won’t live up to my expectations and I’m subliminally sabotaging myself!

    But now that you’ve popped your Metro North cherry, I think you’ll be surprised how many quaint towns are just waiting to be explored! We made it a point to explore outside the city this past summer and we’ve barely scratched the surface ourselves.

    Liked by 1 person

    1. girlingothamcity

      Hahaha, I know, puns are totally your jam! 😉

      I definitely want to go to The Blaze now that I know how easy it is to take the Metro North/get around without a car (that was always my biggest fear). I can’t wait to explore…I said to Kyle that I’d be happy even just making my way up there with a book and hunkering down in a coffee shop to read/work one day!

      As for Horseman’s Hollow, I think you’ll find that it really is fit for a younger crowd 😉 I wouldn’t expect to be too spooked, esp. given your affinity for scary movies!

      Liked by 1 person

    1. girlingothamcity

      Thank you SO much! This is the first year we really went all out, I’m usually pretty low key/don’t like to draw a lot of attention to myself…but participating in the parade was so much fun! We’ve already got some ideas for next year LOL.


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