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New York, the city that never sleeps, is a bustling multicultural metropolis where you can always find something interesting to do that caters to your tastes. But once you’ve covered the most iconic sites, or if you want to lose the crowds, you will need to go beyond the obvious. If you are looking for unusual things to do in New York, these options will surely get you off the beaten path.

For addresses and contact details, click on the map at the end of this post.

Visit the Tenement Museum

For centuries, New York City has inspired the dreams of people from near and far. In fact, since its early days the city has been a magnet for thousands of immigrants looking for a better life. If you have an interest for cultural travel, you should definitely visit the Tenement Museum, located on the Lower East Side.

This historical museum takes visitors back in time to give them a glimpse of what it was like to be an immigrant in New York in the late 19th – early 20th centuries. Housed in a five-story brick building, it is estimated that about 7000 people from over 20 countries lived in this historic site.

Please note that you can only visit the museum by guided tour. Also, photography is not allowed inside the building to preserve the historical atmosphere. And if you want to learn more about New York’s diverse immigrant cultures, join a walking tour that will take you to other unique cultural sites in the Lower East Side, Chinatown, and Little Italy; so that you can taste some amazing food!

Go Wine Tasting in a Rooftop Vineyard

Yes, you read that right. Rooftop Reds is the world’s first commercially viable urban rooftop vineyard. This innovative venue is located in the Brooklyn Navy Yard, a thriving green industrial park built on what used to be one of the nation’s main shipbuilding sites. This area is a hub for sustainable initiatives so it’s well worth a visit, and you can explore it by joining this award-winning tour.


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The first harvest of Rooftop Reds was on October 2017 and the winery currently produces six varieties of wine made with grapes sourced from the Finger Lakes region in upstate New York. Besides wine tasting, you can also come for happy hour, movie nights, summer BBQ’s, and more. To visit the rooftop, you need to reserve in advance.

Go on a Street Art Hunt

One of the best ways to go off the beaten path while traveling is to go searching for street art. New York City has a thriving street art scene that attracts some of the most amazing urban artists from all over the world. If you don’t have time to go searching on your own, you can always join a street art tour, which will not only show you the best artworks but your guide will also give you some interesting background information.

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Take a Break at the Cloisters

This quiet spot in northern Manhattan offers a welcome respite from the hectic pace of NYC. The Cloisters, a branch of the Metropolitan Museum of Art, house the museum’s extensive collection of art and architecture from Medieval Europe. Same day entrance is included for free, when you buy a ticket for the Met. To save time and skip the big line at the museum, it is recommended to buy your tickets online.

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Shop Till You Drop at Brooklyn Flea

Ranked as one of the top markets in the United States, the Brooklyn Flea features over a hundred vendors selling furniture, vintage clothing, antiques, jewellery and much more. If you are looking for the perfect souvenir for your trip, you’ll probably find it here!


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Explore an Abandoned Subway Station

New York’s subway system is one of the oldest in the world. As such, there are a number of stations that were closed or abandoned, for one reason or another. The most famous of them all is the City Hall station and it is possible to visit it by joining one of the tours organised by the New York Transit Museum.

However, scoring a place in one of those tours is nearly impossible for tourists, since you have to be a member of the museum to apply for tickets. But don’t fret! You can at least get a glimpse of the City Hall station and two other abandoned stops from one of the trains, when you book a place on this tour.


Visit MoMA PS1

MoMA PS1 is one of the oldest contemporary art institutions in North America. Affiliated with New York’s Museum of Modern Art, this exhibition space hosts some of the most avant-garde contemporary art in the world.


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Have a Drink and Please Don’t Tell

If you want to revisit what it was like to experience the Prohibition era, you should visit some of New York’s speakeasy bars. One of those bars offering a very unique experience is Please Don’t Tell. To enter, just go into the old phone booth in Crif Dogs, a hot dogs joint in the East Village, and dial the number to get in. Reservations are really hard to get, but recommended. Still, you can always drop by and try your luck to see if there is place available.


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Go Backstage the Metropolitan Opera House

Go where few people have gone before by taking a backstage tour of the Metropolitan Opera House. Held during the performance season, these tours give visitors a glimpse into what goes on in the rehearsal rooms, dressing rooms and stage area.


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Shake it at a Roller Disco

Back in the day, New York used to be a roller disco mecca and even today there are still some hardcore fans that keep on grooving. If you’d like to give it a shot, you should definitely go to one of Lola Star’s Dreamland Roller Disco weekly events in Brooklyn. Every week there’s a different theme around different music personalities and skate rentals are included in the admission price. Also, make sure to dress up for this one!

But if you rather just watch, you can also head to Central Park. Every weekend from April to October, there is a dancing roller skating gathering with live DJs.


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Addresses & Contact Details

If you enjoyed this post, you might also like to read other articles in our Off the Beaten Path series: Paris, London, Rome.

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Unusual Things to Do in New York

What other unusual things to do in New York would you recommend? Share your suggestions with us in the comments section!


  1. Looks like they stopped people staying on the subway through the old City Hall station for a “free tour”. I always wanted to see what it looked like but didn’t want to trespass ?
    Crif dogs is good! Definitely stop for a hotdog.

  2. This list was a joy to look through! I have visited NYC many times and absolutely LOVE the city! I’ve only done about half of the stuff that you’ve mentioned, but the other stuff you have listed looks AWESOME. I’m def gonna try to hit these places up the next time I’m in the city!

  3. Such a great post and it just makes you realise there is SO much more to NYC! The idea of the speakeasy bars sound so mysterious, definitely bookmarking this post for future reference :)

    Char xo

  4. What a nice selection of different things to do in New York! I didn’t even know about the existence of The Cloisters, and that abandoned subway station seems so cool too! Good that you included the map, saved this for when we go to NY!

  5. Uhm, where has this article been all my life?? Seriously, I must have read dozens and dozens of articles on NYC but they are more or less all the same. These things are so unique! I want to do all of them!! <3

  6. Such a awesome post & it just makes you realize there is so much more in New York! The idea of the speakeasy bars sound so mysterious, definitely bookmarking this post for future reference……


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