50 unusual things to do in New York City by a native New Yorker

New York is full of hidden gems. This insider guide to New York City written by a native New Yorker will show you best unusual things to do in New York City that are alternative, kooky, fascinating, and just weird. Buckle up, it’s going to be a wild ride as New York has so much to offer that you might not expect. I’ve grouped these activities by borough and location.

Unusual things to do in Manhattan

Take yourself down to the Lower East Side for a DIY Jewish food tour

An oft-overlooked portion of New York has to be the Lower East Side. This part of New York was once where my ancestors lived when they arrived in New York and it’s long been the Jewish cultural capital of New York. Here, you’ll find all kinds of delicious Jewish foods that you will want to try. Don’t worry, you don’t need a food tour to taste the best of this! Click for my self-guided tour of the best places to eat on the Lower East Side.

Explore the catacombs of St. Patrick’s Basilica

Although many people know St. Patrick’s, however many don’t realize that there’s another St. Patrick’s in New York. Underneath the Basilica of St. Patrick has catacombs underneath. There are very catacombs in the United States and this is the only one in all of New York. The catacombs have been closed for many years, but luckily they’ve now been opened to the public. You can take a candlelight tour of the catacombs to learn more about the history of this epic Basilica!

Sit down for endless coffee and kitsch at a 24/7 diner or deli

One of the most New York experiences off the beaten path that you can have (in my humble opinion!) is to sit at a 24-hour deli or diner and people watch as you get endless refills of black coffee. Veselka (from Nick & Norah) is where you can eat Ukrainian vareniki all night. Similarly, Tick Tock Diner is where my husband (and I have) stopped for a coffee while waiting around for bus near Penn Station. I was recently in Sarge’s Deli, which is a great place to stop off for a proper pastrami sandwich past midnight (or anytime).

Find New York’s hidden streets

New York is full of secrets if you know where to look! My other post about Secret New York goes more into detail about these streets, but I recently was in Henderson Place. This small private street is full of beautiful houses was intended for middle-class people, however, it’s one of the sought-out places to live on the Upper East Side today…

Attend a wild off-off-broadway play for a fraction of a broadway play

One of the best alternative activities in NYC has to be attending and off-off broadway play. Many people assume that you have to attend a Broadway play to get the New York play experience, however at any point, there are dozens of plays in New York that range in topic and you can see one of these plays for very little. Some are a wild experience if you’re open to something new. You can always see the Broadway favorites, but if you look through the TKTS list of shows, you might find something intriguing that you might not have known about otherwise.

Browse the fantastic thrift stores and bookstores for secondhand books

New York is full of beautiful and numerous bookstores. Whenever I’m in the area, I always stop by the Strand for a book, which is easily one of New York’s best bookstores. For shopping, New York is unparalleled and I consider thrifting in New York to be a true art as you have no idea what you’ll find. Click here for my recommendations on the best places to shop on a budget in New York.

Get a drink at a speakeasy

A speakeasy is a bit cliche at this point in New York, but it’s not to say that it’s still cool to enter a hidden bar as something different to do in New York. It’s pretty easy to find most speakeasies online without much effort, however for the full experience and to learn more about the history of these bars, you can take a Prohibition bar tour, which will bring you to New York’s oldest speakeasies.

Discover revolutionary-era New York

New York was once the capital of the United States. Us New Yorkers are proud of everything that started in New York and although we won’t take credit for the American Revolution as much as we do for New York pizza (you’re welcome!), you can visit the exact spot (Fraunces Tavern) where the Sons of Liberty, who help plan the Boston Tea Party plotted. Later on, this was George Washington’s unofficial headquarters. You do have to pay for entry to the museum or you can pay for a meal within the restaurant.

Experience Korean karaoke in K-Town

One of the most fun unusual things to do in New York has to be KTV in Koreatown. Right in the 30s, you’ll find Koreatown, the heart of Korean culture in New York. I recommend looking up KTV bars for the private experience. It’s best to reserve in advance as these bars are quite popular in the evenings on weekends. Within the private boots, you and friends can drink soju (Korean liquor) and belt out your favorite tunes. It’s as much fun as you think!

Find the African Burial Ground National Monument

During a construction project, a mass grave filled with human remains was found in New York. Quickly, it was discovered that this six-acre wide site was the resting place of 15,000 enslaved and free Africans who lived in colonial New York. This monument is the oldest African burial ground in existence. It is free to visit and a great starting place to learn about the darker past of New York. To learn more about the history of slavery and the Underground Railroad in New York, you can take a two-hour tour about the early African American history of New York.

Visit the Tenement Museum

One of my favorite museums for an unusual experience for adults and children alike in New York has to be the Tenement Museum. This museum helps visitors experience what it was like to live in New York at the turn of the century. My own great-grandparents lived in conditions like this and it’s an eye-opener to enter these apartments that are beautifully decorated with accurately represented decor with historians. Reserve in advance! Click for more tips for the Lower East Side.

Attend a free concert/play at Summerstage or Shakespeare in the Park

Every summer, you can attend free world-class plays and concerts in the middle of Central Park. I always love attending Summerstage, which brings many popular music stars from all over the world to New York. Tickets are free. If you’re willing to put up with the lines, you can also line up for New York’s famous Shakespeare Festival, Shakespeare in the park!

Discover New York’s classic bars that haven’t changed in years!

If you’re a fan of Mrs. Maisel, you might be wondering where they filmed many of the classic bars scenes in Mrs. Maisel. Although the new and shiny is always popular in New York, there’s something about the old and worn. There are a number of old historic bars in New York worth visiting, including the White Horse Tavern, which is where Dylan Thomas supposedly took his last drink. I was recently in Old Town Bar (pictured), which was one of the filming locations of Mrs. Maisel. It’s simply a beautiful bar with wooden booths and a cozy atmosphere where the locals chat with those coming in.

Attend a gospel concert in Harlem

One of the most unique things to experience in New York is to experience the richness of African American culture in Harlem. Harlem is truly an incredible place to visit due to the world-famous Apollo, its legacy with jazz music, and its churches. Many others have covered Harlem more in-depth than me, however, it’s worth taking time to see Haarlem whether to visit the Apollo for a show or visit a church for a choir performance. Click for a tour of Harlem!

Enter a European monastery at the Cloisters

One of the best museums in New York for lovers of medieval art has to be the Cloisters. It’s a bit mindboggling to consider that this museum with fairly accurate construction, inspired by medieval monasteries, exists in New York City. Within the museum, you can visit the various sections to look at priceless artifacts from medieval times. Entire sections of monasteries from Spain and France have been moved here although my favorite exhibition had to be the unicorn tapestry. You can get in here free with your Met ticket on the same day. Just include enough time to take the subway or train uptown! I recommend exploring Fort Tyron park after.

Discover New York’s hip hop roots

We say in New York, “East Coast is Beast Coast.” Well, the Beastie Boys were formed in New York. I can’t even list every hip hop and R&B artist from New York, but let’s just keep it simple: Nas, the Notorious B.I.G., Nicki Minaj, Wuu-Tang Clan, Jay-Z, Tupac, and many others are from New York. If you’re a rap fan, consider taking a tour to visit many of the key locations with local artists that shaped hip-hop in New York.

Unusual things to do in Queens

Please leave Manhattan, especially if you’re tired of the same old things. As someone who grew up in Queens, I”m horribly biased, but the rest of this article will discuss unusual thing things to do in the other boroughs! Trust me, you’ll fall in love!

Enjoy New York’s oldest working farm

One of the most unusual places to visit in New York has to be the Queens County Farm. I grew up coming here with my parents and went back here. This working farm is New York’s oldest continuously farmed site (since the 1600s) and you’ll wonder if you’re still in New York City. It’s all the way out by the Queens-Nassau County border, but if you have a car, it’s fantastic for families. The farm itself is free to visit although it’s worth looking up the schedule for the events, which are generally held on weekends. It’s a nice respite from the steel of Manhattan!

Browse LIC Flea

Each weekend, you can browse the LIC Flea Market. This lively market in Long Island City is one of the upcoming cool neighborhoods in Queens where you’ll find lots of cute shops and cafes. Notably, you can browse for locally made products, snack, and head to the beer garden along the water (the East River) in good weather.

Go surfing in the Rockaways

Did you know that you could go surfing in New York!? The Rockaways have been undergoing some massive changes for the better in recent years. For those seeking a truly unusual experience in New York, consider renting a surfboard at the cash-only Rockaway Surf Club. I highly recommend stopping off for some Mexican tacos and a craft beer afterward!

Find Zen at the Noguchi Museum

Not too far from Long Island City, you’ll find the Noguchi Museum. This museum dedicated to zen was once the studio of Isamu Noguchi, a world-renown Japanse-born sculptor who lived in New York. This large museum showcases his beautiful minimalistic models, drawings, and sculptures. I dare say that it’s the most relaxing place to visit in New York.

Taste greek pastries in Astoria!

One of my favorite neighborhoods in Queens is Astoria. If you’re a foodie, you’ll love Queens, which is the home to many New Yorkers who immigrated from Greece. I always love browsing the Greek supermarkets, stopping into the bakeries, and coming here for a meal. Click for my guide to Astoria.

Discover the quietness of Jacob Riis Park and the surrounding abandoned sites

One of the most unusual places that I’ve visited in New York has to be Jacob Riis Park. This beach on the most western part of Queens is not as famous as Coney Island or any of the beaches on Long Island, but it’s absolutely beautiful. I came here in May and we were the only ones on the beach! The old-school beach pavilion is very much old New York although lovers of abandoned places will love exploring the cold war-era Fort Tilton and viewing the former Neponsit Beach Hospital, a tuberculosis sanatorium, from a distance. It’s a nice place for a quiet walk along the beach.

Explore the diversity of Jackson Heights

Jackson Heights is one of those quintessential New York neighborhoods that New Yorkers love. Why? It’s truly representative of the diversity within New York. Here, you can eat Tibetan dumpling before picking up Colombian arepas, Indian snacks at Patel Brothers, or even finding something from another country. Your options are almost limitless as long as you have cash as many businesses are cash only.

Go kayaking in the East River

Have you seen everything in New York? I promise you that you probably haven’t gone kayaking in the East River. I’m not sure that I’d recommend swimming in the water, however you can rent kayaks at the LIC Boathouse.

Eat your way through Flushing

If you’ve not heard of Flushing, you nd to come to Flushing! Although you might have heard of Chinatown, Flushing is at the epicenter of New York’s Chinese community. Here, you can taste Chinese food from various Chinese regions. You can click for my guide to Flushing for the best places to eat in Flushing.

Discover New York in miniature and go around the world 😉

Skip the touristy exhibition in Times Square and head to one of my favorite novelty museum exhibitions in New York, the Panorama of the City of New York! This miniature of New York is absolutely astounding in detail. It’s within the Queens Museum of Art, which sits right around the corner from the world-famous Unisphere.

Discover the Dutch history of New York in Flushing!

Although many have heard the story of how the Dutch settled in New York, you’ll find many traces of the Dutch still here. Queens has several houses that were built when the Dutch ruled New York. My favorite has to be the John Bowne House in Flushing, which traces the rise of religious freedom in North America. The tour, which is affordable, is run by knowledgeable volunteers. I have been to several of the other Dutch-era properties, but I think that this one is the most intriguing!

Dive into jazz history at the Louis Armstrong House

Instagrammers, take note, you can’t take photos within the Louis Armstrong House. However, for jazz lovers, this house is a bit of a pilgrimage location. This home was where Louis Armstrong and his wife lived until his death in 1971. Today, the house is a museum dedicated to his life and music. You must come here with a tour, so please check the official website for more information.

Transport yourself to England in Forest Hill Gardens

Although people assume that New York is all skyscrapers, Queens is full of normal houses where normal New Yorkers live. One of my favorite neighborhoods of New York for a stroll has to be Forest Hill Gardens. Here, you’ll find this Garden-inspired neighborhood full of beautiful Tudors. I recommend enjoying the quiet of Forest Park, a popular getaway in the 1920s for New Yorkers before stepping in for a snack at one of the old German delis in Kew Gardens (Homestead Gourmet Shop).

Take in modern art in Socrates Sculpture Park

One of my favorite free things to do in New York that is a bit unusual has to be gong to Socrates Sculpture Park in Long Island City. This free park hosts sculptures from sculptors from all around the world along this water-front property. The sculptures are always fun to interact with–and enjoy from a distance, so if you’re looking for something different to enjoy, consider bringing a picnic (after stopping by Costco!) to eat in the park.

Enjoy a traditional beer at New York’s oldest beer hall

In the heart of Astoria, you’ll find New York’s oldest beer hall. Although beer halls used to be more common throughout New York, this Czech-run beer hall is still in business 100 years later. It’s a great place to enjoy a beer with a pretzel.

Discover Fort Totten

Fort Totten is where I used to go rollerblading with my mom. This was a key place for defending New York from the British and the Nazis as it’s the entry to New York Harbor. For a long time, there was an army base here (even during the Civil War) and you can view some of the beautiful buildings from this period as you walk around, including the remains of the Civil War-era battery. It’s free to visit although not so easy to get here. The views from the water are gorgeous and worth the trip. It’s a popular destination for runners!

Unusual things to do in Brooklyn

Go antique hunting and enjoy Arabic coffee along Atlantic Avenue

One of my father’s favorite things to do quite a bit off the beaten path in Brooklyn is to stop by the Yemanese coffee to watch chess and relax. Atlantic Avenue has long been at the heart of Brooklyn and you can now enjoy great craft beer at nearby Circa Brewing. If you’re an antique lover, I recommend browsing the antique shops for fun decorations for your home closer to Boerum Hill.

Practice your Russian/Ukrainian and eat vareniki in Brighton Beach 

Brighton Beach is a unique neighborhood that is mostly populated by ethnic Russians and Ukrainians who fled when the Soviet Union fell. Here, you’ll find signs in Cyrillic and food from all over the former USSR from Georgian food to Ukranian vareniki (dumplings). I recently went to Varenichnaya with my cousin, who described it as the most hole-in-the-wall place that he’s ever been to in New York. Don’t worry: They speak English too.

Head underground at New York Transit Museum

Lovers of trains, rejoice! New York Transit Museum is an entire museum dedicated to the history of the New York subway. I’ve been several times when I was younger and it’s really fantastic. I always love boarding the old subway cars, which they occasionally ride on special occasions.

Stroll along the boardwalk on Coney Island and ride New York’s oldest wooden rollercoaster.

I love Coney Island. I’ve been coming here since I was a child. This island off Brooklyn (named for rabbits!) is home to one of New York’s most popular beaches, Nathan’s Famous Hot Dogs, New York’s oldest wooden rollercoaster, cool artwork (for the Instagrammers), an amusement park, and a lovely boardwalk. It’s completely free to visit Coney Island. After you’re done, head to Brighton Beach!

Discover the weirdness that is Gowanus, New York’s very own Superfund site, with a beer.

Have you read about the Gowanus Canal? I’m not sure that New York should be proud of having its very own toxic superfund site, but the Gowanus neighborhood is perfect for those looking to experience the alternative side to Brooklyn. One of Brooklyn’s best breweries is Other Half Brewing Company, so consider grabbing a pint before exploring the neighborhood! History lovers might like the Old Stone House of Brooklyn. For supper, stop at Dinosaur Bar-B-Que for southern-style BBQ!

Find artwork in Bushwick

It’s a bit strange seeing Bushwick gentrifying so much as a New Yorker, however you’ll want to look up the Bushwick Collective. This open-air gallery run by Bushwick local Joseph Ficalora features local artists along with more famous street artists! It’s free to visit and perfect for street art lovers.

Eat your way through New York’s pizza!

Who doesn’t love pizza!? New York is the birthplace of pizza as we know it. Although New York’s old pizza parlor closed, you can head into Brooklyn to Totonno’s to taste pizza at this classic New York institution open since 1924! I was recently at Juliana’s (shown above), which was very tasty. For true foodies, consider taking a pizza tour of New York. Yes, these really exist.

Experience New York’s alternative side at House of Yes

Looking to dance the night away? House of Yes is one of New York’s wildest alternative places to go out. Here, you’ll find great music, a disco bathroom, drag shows, and a fully inclusive environment to dance with your friends.

Discover the insanity of Christmas lights in Dyker Heights

If you’ll be visiting New York in time for the holidays, I recommend taking a detour to Dyker Heights! This charming Brooklyn neighborhood is famous for its epic Christmas light displays in front of the houses! It’s free to visit on your own, however, this neighborhood is a bit out of the way. Consider taking a tour of the best Christmas light displays if you’re not keen on figuring out the logistics.

Unusual things to do in the Bronx

Eat your way through New York’s real Little Italy

Hidden in the Bronx, you’ll find Arthur Avenue. Although you have heard of Little Italy, you need to head this old school neighborhood of the Bronx where Italian culture in New York has been preserved with old school pasta makers, Michelin-starred restaurants serving up incredible pizza, and mozzarella makers worth of the James Beard award. Click for my guide to Arthur Avenue!

Discover Woodlawn Cemetery

If you’re a cemetery lover, you need to head to Woodlawn Cemetery in the Bronx. This notable cemetery built on rolling hills in the Bronx is the final resting place of many famous stars, including Herman Melville and Miles Davis! It’s a bit of fresh air oddly enough in New York and a nice respite from the busy city.

Go for a hike through van Cortlandt park

Not many people realize that you can actually go hiking in New York City. This large park in the Bronx was once the home of the Van Cortlandt family, which still sits on the property. Within the park, you can kayak, hike, run, horseback ride, and even golf. Unfortunately, Robert Moses (one of the urban planners who largely shaped modern-day New York [Read the Power Broker to learn more about his legacy!]) broke up the park and much of the Bronx, however, the park is worth a visit if you think that you’ve seen it all!

Pretend you’re in New England on City Island

City Island is very surprising. This small island off the Bronx feels like New England due to its many seafood restaurants, docks, and the general holiday feeling. The houses here are really cute and trust me when I say that you don’t need to drive another 2 hours to see something different in New York. Consider trying the lobster!

Unusual things to do on Staten Island

Go back in time at Historic Richmond Town

One of the most fascinating places that I’ve visited in New York recently has to be Historic Richmond Town! This open-air museum in Staten Island is full of beautiful homes and shops from different historic periods, including the Dutch-era. Although you can arrive generally anytime, I recommend trying to go on one of the tours, done by knowledgable volunteers in period clothing, which will enable you to enter a few of the houses. We spent several hours here and you cannot get better bang for your buck! (We also recommend the ice cream.) Many TV shows and films were set here, including Boardwalk Empire.

Transport yourself to China within the New York Chinese Scholar’s Garden

One of Staten Island’s unexpected delights has to the New York Chinese Scholar’s Garden. This charming garden was created by Chinse artists and architectures to help bring a bit of Chinese culture to New York. All the materials come from China. Despite its beauty, this garden is not very well-known and right on the edge of the water, so consider coming here on a nice day as it’s the perfect lead-in to discovering that there’s more to Staten Island that just the ferry!

Hike in the Greenbelt and learn about the strange past of this green space!

The Greenbelt is a relatively new part of Staten Island. This park is home to one of the largest green spaces in New York. As part of this space, you’ll find the land that once belonged to the New York City Farm Colony and Willowbrook State School. This former working farm, once the home of Alice Austen (whose home is on Staten Island), has now been taken over by the city. Today, you can walk past some of these semi-abandoned buildings as they figure out what is next for this land (likely condos..)

If you’ve read about the movie Cropsy, Willowbrook State School is one of many urban legends. This institution for those with disabilities became infamous after investigative reports came out, which resulted in the shutting down of this school. Now some of the grounds are part of the College of Staten Island and the Greenbelt.

Other unusual things to do in New York City

Discover the dark history of Ellis Island

Although Ellis Island is famous for immigration, Ellis Island also has some dark stories in its past… Notably, there were separate wards where those who were sick were held prior to being deported. Today, you can tour these “abandoned” sections of Ellis Island. Click for more information about visiting Ellis Island.

Discover Roosevelt island’s dark history!

Roosevelt Island is a strange place, arguably one of the most strange places in New York City. This island sandwiched between Manhattan and Queens has a surprisingly dark history between Blackwell’s Peneiteary, which was shut down after becoming one of New York’s most famous prisons and “lunatic asylums.” It was torn down and now, you’ll find a smallpox hospital (abandoned, but still there) that sits in its place. For the best views of Roosevelt Island, consider taking the tramway for excellent views of Manhattan on the way back!

Meet the friendly cats on Roosevelt Island!

Cat lovers, I haven’t forgotten about you. The Cat Sanctuary in Southpoint Park is a non-profit cat sanctuary on Roosevelt Island where you can visit twenty-two friendly strays that live here full-time. Please consider making a donation if you visit! I got to say hello to one of these kitties when I was on Roosevelt Island recently!

Take an architectural tour of New York by boat

One of the most unusual activities in New York has to be the architectural boat tour of New York that we recently went on! This 3-hour boat tour goes around Manhattan Island and is narrated by a licensed architect in cooperation with the American Institute of Architects.

Review from my dad: I had my doubts about whether it would teach me anything new about my home city of New York. I have an undergraduate degree in History, read The Power Broker by Robert Caro, watched many Ken Burns documentaries, and lived here my entire life. However, I was pleasantly surprised by this tour–and many of the guests were visiting for the second and third time. We also enjoyed the free drink (champagne, wine, water, or soda) and snackers (olives and hummus) that come with the tour.

I could go on endlessly about the Domino Sugar Refinery, Governor’s  Island,  Spuyten Duyvil Bridge, and Roberto Clemente State Park which I had never personally seen.   We had poor weather on the day of our tour and they were happy to switch our tour to Friday. I would highly recommend to anyone who is looking for something different to do in New York.

Any other recommendations for unusual things to do in New York City?

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