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New York, one of the most iconic cities on earth, is a bustling multicultural metropolis that is always ready to impress. If you’ve already seen its most famous landmarks, or if you want to lose the crowds, you should try venturing beyond the obvious. For those looking to experience the most unique side of the Big Apple, these unusual things to do in New York will surely get you off the beaten path.

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

Unusual Things to Do in New York

The Tenement Museum

If you have an interest in cultural travel, you should definitely visit the Tenement Museum, a remarkable historical museum located on the Lower East Side and one of the coolest museums in NYC. Housed in two historic brick buildings, you can visit the restored apartments of some of the immigrant families who used to live there.

During one of the guided tours, visitors go back in time to experience for a moment what it was like to be an immigrant in New York in the late 19th – early 20th centuries. According to some estimates, about 7,000 people from over 20 countries lived in this historic site.

38 of the Best Brunch Spots in NYC

Good to Know

You can only visit the museum on a guided tour. Also, to preserve the historical atmosphere, photography is not allowed inside the building. Some of the most popular tours, tend to sell out; so it’s best to book your tickets in advance. And, if you are traveling with children, keep in mind that most experiences in the museum are only suitable for kids aged six and up.

Finally, for those who want to learn more about New York’s diverse immigrant cultures, this walking tour will take you to other unique cultural sites in the Lower East Side, Chinatown, and Little Italy. The best part of the tour is that it combines rich historical knowledge with tasting some amazing food!

Wine Tasting in a Rooftop Vineyard

Yes, you read that right. Rooftop Reds is the world’s first commercially viable urban rooftop vineyard and one of the most unique things to do in Brooklyn. The first harvest of Rooftop Reds was collected on October 2017. The winery currently produces six varieties of wine made with grapes sourced from the Finger Lakes region in upstate New York.

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 one of the best ways to explore the area is by joining this award-winning tour, which was selected as the Best Tour of 2012 by New York Magazine.

Good to Know

Besides wine tasting sessions, the winery also organizes several activities; such as guided visits every Wednesday, rooftop yoga sessions, brunch on Saturdays, and brewing workshops.

Also during summer, there’s a monthly all-you-can-eat BBQ event and movie nights on Thursday evenings. To visit the rooftop, you need to reserve in advance.

Go on a Street Art Hunt

One of the best ways to enjoy NYC off the beaten path is to go searching for street art. This fantastic city has been at the forefront of the graffiti movement from its very beginning. And, to this day, it is home to a thriving street art scene that attracts some of the most amazing urban artists from all over the world.

Some of the best areas for street art in New York include the L.I.S.A. Project in Little Italy, Highline Art in the High Line, the Graffiti Hall of Fame in East Harlem, the Coney Art Walls in Coney Island, the DUMBO Walls and the Bushwick Collective, which are both in Brooklyn, among other places.

Good to Know

Looking for street art can take time and dedication. If you don’t have much time to go searching on your own, you can always join a street art tour. This way, you can easily see the best artworks while your guide explains some interesting background information.

Photo by Mercedes Álvarez via Unsplash

The Cloisters

Set in a quiet location in Upper Manhattan, The Cloisters are a branch of the Metropolitan Museum of Art. With a monastic atmosphere, this is truly one of the most unusual places to visit in New York and offers a pleasant respite from the city’s hectic pace.

Surrounded by beautiful gardens and featuring a lovely inner courtyard, the building was constructed using sections of French medieval monasteries. Inside, you can admire the MET’s extensive collection of medieval art, which includes many statues, paintings, stained glass windows, and tapestries.

Good to Know

Same day entrance is included for free when you buy a ticket for the Met. If you want o save time and skip the big line at the museum, it is recommended to buy your tickets online.

House of Yes

Set in a warehouse in the heart of the famous Bushwick district in Brooklyn, House of Yes is a place for pure artistic expression. With its Burning Manesque vibes, full-on psychedelic decor, and amazing acrobatic shows; this fantastic club offers you a place to dance your heart out, lose your inhibitions and enjoy a wild night out.

Here, you are encouraged to wear your most out-of-this-world outfit, don plenty of glitter and let your creativity shine. If you are looking for a unique experience in New York, head to House of Yes!

Good to Know

There are different themes happening every night, so make sure to check their program. We highly recommend you buy your tickets in advance to avoid waiting in line or sold-out shows. Before the show starts, you can hang out at the bar. You can only enter the theater area 30 minutes before the show begins.

Keep in mind that almost all events are for people 21 years and older. Cocktails are about $14 USD, which is pretty reasonable for NYC.

New York Transit Museum

New York’s subway system is one of the oldest in the world. And at the NYC Transit Museum, you can see several displays and artifacts chronicling the history of the city’s transport network. It is the largest museum in the United States dedicated to urban public transportation history and one of the best in the world of its kind.

The museum is housed in an old subway station in Brooklyn. One of the best parts is the collection of different subway cars arranged by decade and the display of NYC transportation maps is fascinating. You don’t have to be a train enthusiast to enjoy this hidden gem, plus it’s a great place to spend an afternoon with the kids.

Good to Know

Admission is $10 USD per adult and $5 USD for seniors and children aged two to seventeen years old. The museum is closed on Mondays and major holidays.


With the MoMA being closed from June 16 to October 20, the MoMA PS1 offers a great alternative for those looking for an art fix. This exhibition space hosts some of the most avant-garde contemporary art in the world and is one of the oldest contemporary art institutions in North America.

Located in Queens and housed in a former public school building far away from the bustling streets of Manhattan, this space is affiliated with New York’s Museum of Modern Art. Most of the art on display is an eclectic mix of up-and-coming artists.

Good to Know

In summer, they hold the Warm Up events, which showcase the best in live and electronic music. The events take place every Saturday in July and August.

The museum is closed on Tuesdays and Wednesdays. Opening hours are from 12:00 pm to 6:00 pm. Admission fees are $10 USD for adults, $5 USD for seniors and students (ID required), and free for children under 16 and NYC residents.

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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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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