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Greetings Internet Stranger and welcome to 24 hours of the best things to do in Ossining, NY and Croton-on-Hudson! When most New Yorkers think of the best Things to Do in Ossining NY, they might imagine a crime had been committed. After all, Ossining is most famous for the notorious Sing Sing Prison.

But don’t let that stop you from giving Ossining a try! The best Things to Do in Ossining NY are just a short train trip away from New York City, and it’s a lovely place to spend a morning, especially on a crisp fall day.

Croton-on-Hudson is even less well known than Ossining, but it becomes a major attraction every fall. That’s when the town opens its doors to the magical Great Jack-o-Lantern Blaze. You can’t find a more perfect 24 hours in New York State than a weekend trip to these adorable towns. Escape the rat race of New York City and see some truly freaky pumpkins while you’re at it!

Things to Do in Ossining and Croton-on-Hudson

What to Pack

Things to Do in Ossining NY and Croton-on-Hudson: A Perfect 24 Hours 3

You’ll also need comfy shoes for all the walking we’re going to do. If it’s summertime, I love my special pink Birkenstocks. These aren’t your grandpappy’s Birkenstocks anymore. They come in every shade, and I always get compliments on my electric magenta shoes.

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If the weather is rainy or snowy, which happens quite often in NY, I recommend the Asgard Rain Boots. They are comfy/cozy and keep my feet dry all day. Plus they’re cute enough that I can wear them out without feeling like some gauche tourist with gross feet.

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Finally, since we’re going to be out all day, you’ll want a battery for your cell phone. I always use the Anker charger. It’s light enough to fit in even a small purse. Plus the Anker lasts for several full charges of a phone, so I’ll never run out of juice!

Things to Do in Ossining NY

Things to Do in Ossining NY and Croton-on-Hudson

Morning: Explore Ossining

Ossining has two main claims to fame. As I mentioned, it is the home of the highly controversial Sing Sing Prison. Second, it is the home of Mad Men‘s Don and Betty Draper. But Ossining is so much more than just the residence of assorted convicts and fictional philanders. It’s also home to tasty food from a surprisingly wide variety of countries and exquisite turn of the century architecture. Just take a Metro North train from New York City, and you’ll be in Ossining in under an hour.

Fortunately, the Village of Ossining seems a little on the ball, tourism wise, and has a handy free self-guided walking tour that will help you explore the best Things to Do in Ossining NY. But I’ll point you towards the very best with…

approximately top 5: Things to Do in Ossining NY

24 hours in ossining
1) shopping!

Ossining used to be famous for the shops on its Main Street. During the 1970s and 80s, the village went in to a bit of a decline, and many of the shops closed. But locals kept telling me that things were starting to pick up, and every time I spend 24 hours in Ossining, I notice that new shops and restaurants have opened in town.

If you’re in Ossining on a Saturday, be sure to visit the Farmers Market. You’ll find only New York State businesses selling prepared foods and produce as well as “talented” locals strumming on their guitars. Ossining is home to a largish Central American community. I recommend at least grabbing a cup of coffee at the Xquisite Coffee Plantation stand, run by a lovely Guatemalan-American family. The apples and honey at the Mead Orchard stand are excellent as well.

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If the Farmers Market isn’t open, you can still include shopping as one of the Things to Do in Ossining NY. My favorite store is Melita’s Home. She sells everything from home furnishings to jewelry to baby clothes. If you’re an obsessive earring collector like me, you’ll want to pick up a pair from a local artist here. But I also highly recommend her beautiful oil and vinegar cruets and olive plates, all handmade in Portugal.

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2) ossining churches

For such a small village, Ossining is home to a large number of churches. They’re definitely some of the best Things to Do in Ossining NY. I know some people are not into church architecture. And I confess I find it so interesting that my own sister has called me a “Church-a-holic”. But you don’t need to be religious to have a blast churching! Allow me to give you a few tips.

his church above, the First Baptist Church, is in the Victorian Gothic style. This means that there’s a lot of pointy shapes and probably a psychotic priest who’s hiding a hunchback somewhere in a tower.

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This church is also Victorian Gothic but it is a Presbyterian Church, not a Baptist Church. Presbyterians follow the theology of John Calvin, which I think means that they need to speak Swiss and believe that there’s nothing you can do to be saved–God has already chosen who’ll be going to Heaven and going to Hell before you are born. So you might as well just throw raging parties all the time, since your fate has already been decided. That’s where the saying “Ain’t no party like a Presbyterian party” comes from.

See! Church exploring is very fun if you’re willing to take a little bit of knowledge and go to some crazy places with it.

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3) ossining visitors center

The Ossining Visitors Center also serves as a little free museum. It’s the perfect place to go if it’s raining, but you still want to find Things to Do in Ossining NY. The museum has exhibits on Ossining’s two most famous features: Sing Sing Prison and the Old Croton Aqueduct. The section on the Aqueduct is called Down the River and the section on Sing Sing is called Up the River. Clever!

The phrase “getting sent up the river” comes from Sing Sing because convicts from New York City were sent up the river to Ossining to serve their sentences. The exhibit on Sing Sing is stuffed with information about prison life. I never knew that solitary confinement was developed as a more humane punishment than being kept with other prisoners. It was supposed to give prisoners time to meditate and it…did not work.

On the more gruesome side, the Ossining Visitors Center also has a collection of items that prisoners have turned into weapons. So if you’ve ever wanted to see a shank made out of a pen or a plastic fork, now is your chance.

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4) lunch at cravin

At this point in our search for the best Things to Do in Ossining NY, we’ll be wanting lunch. So let’s stop at my favorite restaurant in Ossining, Cravin. Cravin is owned by a local Jamaican-American named Peter Murdoch. He opened the restaurant because he didn’t like having to go into New York City to get Jamaican food.

I love Cravin because they have so many different options depending on how adventurous you are feeling. You can get oxtail or goat curry (my personal favorite). But they also have chicken and vegetarian options. I also recommend their homemade juices, especially the sweet and spicy sorrel juice. It will temporarily stain your tongue purple, but it will be worth it.

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5) old croton aqueduct

You can’t make a list of the best Things to Do in Ossining NY without seeing the Old Croton Aqueduct. The Aqueduct is basically the oldest thing in Ossining, as it was built between 1837 and 1842. Martin Van Buren, our eighth president, was in office when they started building this aqueduct, that’s how old it is. Its job was to bring water from the Croton Aqueduct all the way into New York City. So Ossining sends us fresh water and we send them prisoners. Not sure that’s a fair trade!

My favorite fun fact about the aqueduct is that Washington Irving, the famous author of “The Legend of Sleepy Hollow” and “Rip Van Winkle” could hear them building the aqueduct from his house. He claimed in a letter to a friend that the young Irishmen who were building the aqueduct were scared of goblins living in the woods around the aqueduct.

I kind of feel like he was making the whole thing up, as both Washington and I have pretty impish senses of humor. But if you find goblins in the woods, please send me pics and I will post them on the blog!

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Things to Do in Ossining NY and Croton-on-Hudson

Afternoon: Croton-on-Hudson

Croton-on-Hudson is a little sleepier and more spread out than Ossining. But there’s still plenty to do here if you have a spare afternoon, especially if you like evening and walking as much as I do. Plus, if you’re in the Hudson River Valley in the autumn, which you really should be, Croton-on-Hudson is the only place where you can take in the majestic Jack-o-Lantern Blaze!

But as the Blaze doesn’t start til nightfall, I’ll keep you busy as we explore with…

three fun facts: croton-on-hudson

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1) how do I get to croton-on-hudson?

With your feet! I did say there’d be lots of walking. It’s very easy to walk from Ossining to Croton-on-Hudson. Google Maps will show you how to get from one town to another no problem. And you’ll get spectacular views of the Hudson River without having to pay for a boat rental or such-like. Plus you’ll be able to stop at a friendly neighborhood gas station on the way if you need a restroom stop.

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Once again, I strongly urge you to follow this itinerary in the fall. Look at that New York State fall foliage. I’m biased because New York is my home state, but I think New England can suck it when it comes to leaf peeping. We’re the best.

If you’re not up to walking, just take the Metro North train from Ossining to the Croton-Harmon station. (Yes, the Croton-Harmon station is the station for Croton-on-Hudson. It’s like they’re trying to confuse you.)

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2) what is there to eat in croton-on-hudson?

We just had a big Jamaican lunch, but after all that walking, you’re probably hungry again. No matter what the temperature is like, you’ll want to stop at the Blue Pig for ice cream. All the ice cream is handmade with local ingredients, sometimes even ingredients from the Blue Pig’s own farm! This is as fresh as it gets.

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I suggest getting the sampler, so you can try two different flavors. The flavors change with the seasons, so if you’ve been listening to me and you’re visiting in the fall, I suggest combining maple walnut with candy corn. The maple is the real stuff and not too sweet. The candy corn ice cream is perfect because you get the sugary taste of candy corn without the waxy texture. It’s the perfect Halloween ice cream flavor.

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The other Colored Animal food place I recommend in Croton-on-Hudson is Black Cow Coffee. There’s lots of seating, so you’ll be able to sip your cuppa joe and relax for a while. Their house specialty is the creamy Black Cow mocha. But you can get pretty much any type of coffee your heart desires. There’s even a cute little gallery/shop attached in case you didn’t do enough shopping back in Ossining. (Yes, I bought a pair of earrings. Do you even have to ask, Internet Stranger?)

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3) what’s there to do in croton-on-hudson?

Gosh, Internet Stranger! Can’t you just be content with some delicious ice cream and coffee? Does everything need to be a major activity? Croton-On-Hudson doesn’t have museums or anything, but there are some lovely places to walk, read a book, and enjoy the colorful leaves.

If you’re not too easily spooked, I recommend taking a walk in Bethel Cemetery. It’s on a hill, so there’s great views of the entire town on a clear day. Just be on a lookout for those goblins that Washington Irving was talking about! I’m very serious about wanting your photographs.

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Duck Pond Park is the other main scenic spot in Croton-on-Hudson. I personally think they should name it White Duck Pond to go with Blue Pig Ice Cream and Black Cat Coffee. Then someone could write a book about the duck, the pig, and the cat becoming friends. But the Croton-on-Hudson tourist bureau won’t listen to me and they won’t return my calls anymore. I’m not going to be IGNORED, Croton-on Hudson!

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Things to Do in Ossining NY and Croton-on-Hudson

Evening: Great Jack-O-Lantern Blaze

The Great Jack-O-Lantern Blaze is the major event of the year in Croton-on-Hudson. Basically the historic Van Cortlandt Mansion gets turned into the world’s greatest open air carved pumpkin museum. It runs every autumn, and it’s so popular that tickets regularly sell out, especially on weekends.

So buy your tickets as far in advance as you can on their website. If you’re a member of Historic Hudson Valley, or if you’ve bought tickets to the blaze before, you’ll get invited to buy tickets before the general public can, which is great if you want to visit on a really popular weekend.

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24 hour treat: eatalia on hudson

Whether or not you’re seeing the Jack-o-Lantern Blaze, I suggest grabbing dinner at Eatalia on Hudson. It’s just a short walk from the Jack-o-Lantern Blaze, and the staff is very familiar with getting people out on time for their Blaze tickets.

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But even if you aren’t visiting Croton-on-Hudson in the fall, I still recommend getting dinner here. Their fresh butternut squash, sage, and butter ravioli is as comforting as an old sweater knitted by Washington Irving out of goblin fur.

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The Jack-o-Lantern Blaze tickets are timed, so walk on over a few minutes before your ticket time. You don’t need a car; helpful traffic guards are there to guide you on your walk even if it’s dark out. The majestic designs change every year, so I can’t guarantee what you’ll see. But I can share with you my…

approximately top 5: Jack-o-Lantern Blaze

24 hours in ossining
1) masterpieces of pumpkins

They have Pumpkin “The Scream” and Pumpkin Frida Kahlo. This one I like to call “Pumpkin Andy Warhol”.

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2) pumpkin sea serpent

There’s no actual sea here, so maybe he should be called the pumpkin grass serpent?

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3) Pumpkin emoji

Can you spot the poop emoji?

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4) pumpkin horoscopes

Gemini for life, y’all!

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5) pumpkin cemetery

If someone would promise me a tombstone like this, ornate and carved out of pumpkins, I might not be so annoyed at the thought of dying someday.

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6) pumpkin zee bridge

This is the piece de resistance of the Jack-o-Lantern Blaze because you can actually walk over it. It was named after the old Tappan Zee Bridge, which has been replaced with the Mario Cuomo Bridge. So I think they should rename this baby the Pumpkin Cuomo Bridge. Who’s with me?

Once you’ve seen all the pumpkins your heart needs, head to the Croton-Harmon train station, remain confused about why it’s not the Croton-on-Hudson station, and return home with visions of jack-o-lanterns dancing in your head.

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That’s the best Things to Do in Ossining NY!

What do you think are the best Things to Do in Ossining NY and Croton-on-Hudson? Do you agree with me about the Pumpkin Cuomo Bridge? And who will be the first to send in their photos of assorted hibernophobe goblins? Please leave your thoughts below!

Note: If you want to know how I put my travel itineraries together, just click here. If you have more time in the Hudson River Valley than just 24 hours of the best Things to Do in Ossining NY, try spending 24 hours in Tarrytown as well. Or you could make time for 24 hours in Beacon. I’ve got you covered either way!

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