The truth is, if you went to Manhattan and stuck your itinerary to just all the tourist hubs and attractions like Times Square and the Statue of Liberty and Central Park, you would probably think, “This isn’t so cool? What’s so cool about Manhattan?”
What is cool about Manhattan? Depends on your definition of cool. That’s what’s so cool about Manhattan, it is a collection of neighborhoods that are so diverse and different that one of them is bound to have the kind of cool you’re after.
Manhattan is actually an assembly of cool little neighborhoods and this article is going to tell you which of those are the coolest neighborhoods in Manhattan.
Borough Number One
Manhattan, the center of the greatest city in the great state of New York, and some may argue the greatest city in the world, is actually an island! That’s right, no man is an island, but Manhattan is.
Manhattan is one of five boroughs that make up the entire region known as New York City. Besides Manhattan, there is Brooklyn, Queens, The Bronx and another island, Staten Island. Brooklyn and Queens can be reached by bridge and The Bronx by underground subway. For Staten Island you’re going to need a ferry.
This article will concentrate on the first and most important of the five boroughs, Manhattan.
How It All Began
Before evolving into the metropolis it is today, the island was home to fishing and hunting grounds occupied by the Lenape Indian Tribe. The territory was first visited by the Italian explorer Verrazano in 1524 but not settled until the Englishman Henry Hudson came along in 1609. Hence, landmarks such as the Hudson River and the Verrazano Bridge.
By 1624 Dutch fur traders had staked a claim, calling the area New Amsterdam. Then, famously, in 1626 the land was bought from the tribe for goods valued at just around twenty-five dollars, or about one thousand adjusted for inflation today.
The rest is history, as they say. Now enjoy some fun facts!
- Did You Know? Manhattan was abandoned during the Revolutionary War and used as a British military center.
- Did You Know? Manhattan used to be the capital of the United States.
- Did You Know? New York City was officially divided into the five boroughs as we know it today in 1898 during a period known as consolidation. Previously, the territories had belonged to other counties or were a county of their own, as in the case of Queens.
Coolest Neighborhoods in New York
Ironically, Manhattan is the geographically smallest but most densely populated borough of the group. Time to take a closer look at the cool neighborhoods that form the rich tapestry of the world’s greatest island.
Battery Park City
Battery Park City is on the west side, bound by the Hudson River and Hudson shoreline on the north, south and west, and the West Side highway on the east.
Primarily a waterfront neighborhood, Battery Park City has a number of attractions and is named for Battery Park, which is in the southern part of the neighborhood and a crown of the city parks department’s jewels.
If aqua is your definition of cool, Battery Park is for you. The waterfront is actively maintained and there are all sorts of activities. You can go kayaking, stand up paddling and swimming. For ground dwellers, a skate park and the ancient Castle Gardens, one of the first immigrant depots.
That’s part of what makes Battery Park City so cool. The feeling of outdoors in the middle of sprawling urbania. There is free yoga in the park and a basketball court, plus pedestrian walkways.
The nightlife is equally natural and low-key. Rooftop bars offer spectacular views. The city’s rich cultural history is reflected at the first beer garden in America and in speakeasies found in old bank vaults. And with the waterfront nearby, the seafood at area restaurants is abundant.
Battery Park City is the coolest place to be when the warm weather comes around. Famous residents like Leonardo Dicaprio, Sacha Baron Cohen and Tyra Banks would surely agree.
Chinatown is on the Lower East Side and is bordered by Broadway on the west, Canal Street and Grand Street on the north, Essex Street on the East, and Henry Street on the south.
Be aware that it can get a bit confusing directionally in the lower depths of Manhattan. It’s not the traditional grid like the rest of the city, which is much easier to navigate. You can get lost in an instant, so stay sharp. This is New York City – nobody’s gonna do it for you!
Chinatown is one of the most authentic neighborhoods in New York City. That’s what makes it so cool. It’s tiny but it packs a lot of punch. In fact, it’s so authentic the streets all have Chinese letters displaying their names along with the English.
Of course, the food is the main attraction, because it is so authentic. The main artery of Chinatown cuisine is Mott Street and you can sample everything from dim sum to dumplings to noodles and more.
With a Buddhist Temple as one its anchors, Chinatown is for people who know that the ultimate cool is Zen.
The East Village is arguably the epitome of cool. Or at least it was. And might still be.
East Village is east of third avenue and actually comprises three cool neighborhoods all worth checking out – The Bowery, Alphabet City and Little Ukraine.
Alphabet City is so known because that’s where the avenue names change from numbers to letters. Avenue A. Avenue B and Avenue C. On Eighth Street from Second to Third avenue is one of the coolest streets in Manhattan – St. Marks Place, where the underground scene of New York bohemian artists flourished and still rocks to this day.
The East Village became cool in the fifties and the sixties when the beatnik culture invaded the area looking for refuge from ever more expensive Greenwich Village. It was the center of counterculture and birthplace of punk rock.
The Bowery is a special home for artistic types. The legendary club CBGBs was in The Bowery. The neighborhood has changed – now the club is a designer menswear boutique.
Little Ukraine is up and coming, although it’s not so Ukranian anymore. There are a number of cool hole-in-the-wall ethnic joints to explore.
The East Village will never go out of style! Roam the streets of the village and pretend you’re a punk rocker going wild in the swingin’ seventies.
Si, amigo, El Barrio. El Barrio runs from 96th street to 143rd street on the East Side, bordered by Fifth Avenue and the East River on either side.
Ever heard the melodic refrain “There is a rose in Spanish Harlem”, most famously sung by the Queen of Soul herself, Aretha Franklin. Spanish Harlem is the other name for El Barrio and both are nicknames for East Harlem. Nothing cooler a neighborhood can do than inspire such a timeless classic!
East Harlem is a hot neighborhood with a rich cultural history that is in the process of gentrifying. It’s got such a rich cultural history that it has its own dedicated museum, El Museo Del Barrio.
It’s cultural heritage is one reason that it is still such an artistic neighborhood. Graffiti by famous artists can be found dotting the neighborhood.
Then there is the art of cuisine. East Harlem offers diverse ethnic foods from the Carribean and Latin America.
So many icons hail from East Harlem, including some of the most legendary contributors to musical culture, including Tito Puente and Tupac Shakur.
El Barrio doesn’t have to tell you why it’s chevere, it’s right in your face. And you just learned how to say “cool’ in Barrio!
But don’t count out the rest of Harlem. The rest of Harlem is just west – duh – of East Harlem. A nice way to get there is to cross Central Park, actually. You will come out on 110th Street and Central Park West.
Harlem proper runs up to roughly 148th street from 110th street and is bordered by Riverside Drive, ending around where Manhattan borders The Bronx.
The rest of Harlem ranks arguably even higher on the coolometer than its Eastern brother and on the cultural scale. The world renowned Apollo Theatre is in Harlem. The theatre hosts an amateur night where superstars like Billie Holiday and Michael Jackson made noise at the start of their careers.
The rest of Harlem has delicious dining and ebullient nightlife. An indulgent soul food extravaganza can be followed by live jazz long into the night. During the day visit the Graffiti Museum.
Harlem is so much the definition of cool there should be a picture of it next to cool in the dictionary.
Hells Kitchen. Not as scary as it sounds. Well, not anymore. Since Marvel’s Daredevil cleaned it up. Did you know? It’s named after the famous biker gang “Hell’s Angels”.
Hell’s Kitchen runs from 34th Street in Midtown Manhattan to 59th street on the far West Side, bordered by Eighth Avenue and the Hudson River. It’s prime location – you are just a jump from Lincoln Center and the best parts of the Upper West Side and around the other corner is Times Square, Broadway and Penn Station.
Hell’s Kitchen is where you find many of the best Off-Broadway theatres, where some of the most exciting and coolest theatre is going on. Many of these shows, if successful, will move to Broadway. But you can see them here first!
Koreatown is also in Hell’s Kitchen so you can chow down on authentic Korean Barbeque. Besides that, there’s all other kinds of world cuisine to wet your pallet.
Many classic movies set in New York City have been filmed in Hell’s Kitchen including ‘The Godfather’, “Raging Bull”, “Sleepers”, as well as the recent Netflix Marvel comic series “Jessica Jones”. You’ll want to hang around Hell’s Kitchen long after you’ve expired!
Kips Bay is sort of the East Side, bizarro version of Hell’s Kitchen, though certainly not as well known. Kips Bay runs from 23rd street to 34th street on the East Side, bordered by the East River and Third Avenue.
Kips Bay is more residential and way less gritty than Hell’s Kitchen. Originally a colonial settlement, it is now populated by a number of high-rise apartment buildings. Kips Bay is very low-key, especially by Manhattan standards. It has a low-key cool.
It also has a higher percentage of college graduates, so Kips Bay is not just cooler, but smarter too. One of the main attractions is Kips Bay Plaza, which hosts one of the most spacious multiplexes in Manhattan. One of the local libraries dates back to 1887.
You’ve got hip underground comedy clubs and old school pinball arcades, plus the waterfront where you can enjoy a peaceful walk by the water and great views of the bridge.
In Kips Bay you have your choice of Mexican, Indian or pizza food amongst other flavors. So if your idea of cool is a nice dinner, a movie and then getting curled up all cozy on the couch with a book in your comfortable residential complex apartment, Kips Bay is the coolest neighborhood for you!
Little Italy is not just cool, it’s bellissimo! Little Italy is small and getting smaller, but the piece of Manhattan history it represents looms large.
The boundaries of Little Italy in present days are bordered by Canal Street south, the aforementioned Bowery to the East, and Lafayette street to the West.
Little Italy is decorated with tenement houses that immigrants used to inhabit and even a few cobblestone streets remain intact for a blast from Manhattan’s past. Little Italy is home to the hideouts and meeting spots of the famous Italian gangsters known as the “Mulberry Street Mafia”.
It’s also got New York’s first pizzeria, Lombardi’s on Spring Street, which opened over 100 years ago in 1905. Although some people will argue with you about whether the Italian’s really invented pizza. In any case, Lombardi’s brought the Neapolitan!
Most of the restaurants on Mulberry Street are like walking into a mafia movie. Be careful with that cannoli!
If for you molto bene cool means pretending you’re a gangster bootlegging in prohibition, get yourself to Little Italy!
Lower East Side
The Lower East Side is known by the cool kids as LES. It is one of the last Manhattan neighborhoods that could be called “inexpensive” while also proudly wearing the merit badge of most multicultural.
History is here. There’s a tenement museum that will show you what living there was like back when Manhattan was still being built into the world famous destination it is today.
Manhattan is famous for its delis. And the most famous New York deli, Katz’s, is on the Lower East Side. Besides it’s revered pastrami sandwich, Katz’s is where the famous “I’ll have what she’s having” orgasm scene from “When Harry Met Sally” was filmed here.
Also pop by the Essex Street Market, which is noted for its food stands.
The Lower East Side is stuffed with trendy art galleries and sleek rooftop bars. But the best view you will find is from Pier 35 on the waterfront, where you can sit and ponder Manhattan from the comfort of the free public swings.
Finally, what makes Soho one of Manhattan’s coolest neighborhoods is its chic artistic style and community. Soho was once known as “Hell’s Hundred Acres” – not too far from the kitchen – and evolved into an artistic cluster hub.
It used to be a primarily industrial area known as the Cast Iron district and is now officially classified as a historical district. The manufacturing factories were eventually converted into artists lofts, like in all those cool eighties movies about New York City artist types.
SoHo is short for South of Houston Street. The descriptive term was coined in 1962 by urban planner Chester Rapkin. Houston Street is it’s northern boundary. Canal Street is the southern boundary. It’s East and West boundaries are subject to a little dispute.
During prohibition, SoHo hosted a number of speakeasies disguised as legitimate businesses. Today, SoHo is one of the trendiest neighborhoods in Manhattan, filled with boutiques and galleries and fancy food offerings.
It’s more humble cousin, NoHo, which naturally stands for North of Houston, is also a very cool hood to step into, seeing as how it is right next door.
Other New York Neighborhoods
There are a few runner up neighborhoods worth mentioning before this article comes to a close:
Tribeca is an upscale cool neighborhood in lower midtown Manhattan. Tribeca stands for “Triangle Below Canal”.
It’s actually a quadrilateral and its four boundaries are Canal Street, West Street, Broadway, and Chambers Street. Leonardo DiCaprio calls it home, along with other celebrities like Scarlet Johanson, Justin Timberlake and Meryl Streep.
Tribeca’s biggest claim to fame is probably Robert De Niro’s famous Tribeca Film Festival, which he founded in the aftermath of 9/11 to lift the city’s spirits and reinvigorate the neighborhood. There are a lot of cool underground clubs in Tribeca because of all the old warehouses.
The Museum Mile stretches for about a mile along Central Park East on the Upper East Side. Pricey, of course, but culturally significant and if you can snag an apartment, great views of the park.
The Museum Mile earns its name because along the walk are the world famous Guggenheim Museum and MoMa, the Metropolitan Museum of Art, among others. Along this mile you can take in over 2 million works of art! And it’s just a hop, skip and a jump into a stroll through Central Park.
The Meatpacking District holds old New York charm and recalls yesteryear. The High Line, an old elevated railway converted into a garden high above the city runs through the district and there are a lot of cool underground clubs because of all the still-standing warehouses. You might remember that from classic episodes of the hit HBO series “Sex And The City”.
Chelsea is like the hipper cousin of Tribeca. Chelsea is also a waterfront based neighborhood with an active party nightlife. Part of Hudson Yards is in Chelsea and so is the Chelsea Market, where you can pick up fresh fish, pasta and vegetables.
Now get out there and find your cool Manhattan!
Born and raised amidst the hustle and bustle of the Big Apple, I’ve witnessed the city’s many exciting phases. New York is not just a city to me; it’s a living, breathing entity. When I’m not exploring the city or penning down my thoughts, you can find me sipping on a cup of coffee at my favorite local café, playing chess or planning my next trip. For the last twelve years, I’ve been living in South Williamsburg with my partner Berenike.