a taste of: sleepy hollow
a perfect fall day trip from nyc
Halloween has never been my favorite holiday, so it feels slightly out of kilter for me to say visiting Sleepy Hollow has become one of my favorite annual traditions. But it has! It’s a village along the Hudson popularized by Washington Irving’s The Legend of Sleepy Hollow, inspired by the ghost stories he collected throughout his time there. I like that it still feels a little old school compared to other Hudson Valley getaways. It’s unpretentious and very doable in a day if you’re looking for a quick escape from the city.
I’m less here for the lore and more so for the vibes. Think little ghosts and pumpkins à la cute Halloween.
getting there
The first time I came to Tarrytown was mostly on a whim in 2021. Red (Taylor’s Version) was just released and I was itching for a city escape, so I picked the closest stop on Metro North for a wistfully dramatic train ride.
Okay, some logistics. Aside from coffeeshops, most stores don’t open until 11am. Most are closed on Mondays or close by 4pm, so aiming for 9:30am departure / 5pm return is perfect unless you want additional time to explore the cemetery. If you catch an express train from Grand Central, it takes just 40 minutes to reach Tarrytown. (It’s still under an hour with a non-express.) Maybe arrive a little early to grab a coffee at Joe’s downstairs and have your Serena moment in the main concourse. Use the TrainTime app to buy your ticket on board: it’s $11.25 for an one-way, off-peak ride. Be warned that this is the same train line for Beacon, so it’ll likely be crowded on a weekend with groups headed to Fishkill Farms and the like. (Tip: If it’s really busy, the conductor won’t check your ticket, so don’t feel the need to buy/activate yours too early.)
main street
From Tarrytown station, it’s about a 10 minute walk uphill to Main Street. If you’re ready for a caffeine fix, you’ll reach Muddy Water Coffee first. They have a backyard and it’s never too hard to find a seat—I’ve camped out for some quiet laptop work here. They also have a fun collection of I Spy books. Alternatively, Coffee Labs Roasters is at the end of the street: great coffee, mid pastries, will probably have a line. You can easily spend an hour or so popping in and out of the stores on this street. Some of my highlights, in walking path order:
Trilogy Consignment is well organized with a small designer-only room in the back.
Main Street Sweets has everything you expect out of a small-town ice cream shop: high schoolers serving you scoops behind the counter, and every combination of dessert and coffee possible.
Transom Bookshop is one of the newer establishments on this block. Nicely curated and aesthetically more similar to Hudson Valley shoppy shops.
Tarrytown Music Hall, identifiable by its old-school marquee sign, has a volunteer-run record store upstairs with a huge vinyl and CD selection. All profits benefit the music hall. Wholesome! (Someone please come with me to their Rocky Horror show next year.)
Stop in Carol Master Antiques across the street if you’re seriously shopping for antiques and have a car to bring any finds back with you. At least say hi to the sweetie black lab!!
As for food, nothing really stands out (and we’re picky, coming from the city). But there’s at least one option per cuisine for you to choose from: sushi, gyros, burgers, tacos.
two roads diverged…
…if only briefly. At the end of Main Street, you can turn right for a slight detour down to Pretty Funny Vintage, a Victorian yellow house with a mix of home goods and fun knickknacks.
Otherwise, go left towards Sleepy Hollow proper. It’s about 25 minutes walking to the main cemetery. Pop in the The Swan’s House (think gold accents, pastels, 60s-80s vintage) and maybe Horsefeathers for lunch. They don’t take reservations—we put our name in around noon and waited a little over an hour before we were seated, so make this your first stop after deboarding the train if you’re determined to not wait. People flock here for its perfect grunginess of worn-in booths, wooden walls, and suburban mom level of decor. The food is pretty decent, minus the fries. The waitress also told us it’s way less hectic after Halloween and they swap out all the decor for Christmas. I guess we’re coming back in December…!
If you’re in town on a Saturday, you might catch extra festivities like the local farmer’s market or Halloween parade. Last weekend we even stumbled upon the public library book sale. Otherwise, you’ll continue on to Phillipsburg Manor, which you can tour or simply admire from afar via this bridge:
There’s a perfunctory Headless Horseman statue around here. Feel free to skip it and just route to the small Dutch church at the bottom of the cemetery. They run group tours, but you can grab a free map and make your own way to major gravesites like Irving, Rockefeller, and Carnegie’s gravesites. (Here’s a more thorough walkthrough if historical context and landmarks are more of your thing. I’m more of a walk-around-and-try-to-learn-on-the-way person.) It’s quite peaceful here: not too crowded or empty, more charming than eerie. The cemetery gates close at 4:30, so you also can’t linger too long after dark.
For a different path back to the train station, take Beekman Ave instead of Main Street. I generally prefer going back to the city for dinner, but if you’re not in a rush, there’s a number of bars and restaurants on this street or down by the water (see Bridge View Tavern). Last year we stopped in Croqueteria to pick up some warm croquettes.
In summary, Sleepy Hollow has the correct autumnal energy:
Thank you as always for reading! More thoughts from October in the next letter, but you can also find me on IG for more consistent glimpses into life. Happy Hallo-week! 🎃 x