This article contains affiliate links. If you click and make a booking I will make a very small commission paid by the booking company at no additional cost to you. Thank you for stopping by!

crazy things to do in new york main

Times Square, Central Park, Fifth Avenue. All great tourist attractions but what about exploring other alternative and hipster things in New York City?

After visiting a few times, I wanted some of the cheesy Hollywood experiences and also some of the cooler options as well. After my friend living there, bless her, took me to the very spot in Central Park where one of the characters of Gossip Girl (remember the series about all those rich and spoiled girls?) used to go to feed the ducks, (I can’t remember the name of the actress or the place) my dose of Hollywood had been filled, so I was craving something more interesting. And nobody does Hipster like New York.

The city is the center of creativity, innovation and crazy ideas. Any hipster concepts start in the city that never sleeps. Let it swallow you into the world of La Mafia, crime TV series, fascinating stories, rich cultural heritage, great parks and examples of out-of-the-box thinking in this guide to the few fabulous, alternative and crazy things to do in New York.

Do the hipster things in New York City, let go of your inhibitions, then head to some of the most unusual places by the hand of this alternative guide to New York city. Many has been written about the typical tourist spots so I will only show you the more interesting side of New York, the one that goes under the skin of the city and brings you its most interesting sights.

Nobody does hipster living like New York City.

Hipster, alternative and crazy things to do in New York

1. High Line


New York high line

New York high line

Although no longer a novelty but more of a well-established destination, the High Line always has something to keep one coming back and is an iconic hipster symbol of New York City.

The High Line is an elevated park built along the old train tracks it offers regular music performances, shopping, food, drinks and evenings out in the summer. Walk along its entirety for the full experience and make sure to allow for enough time to chill with a book on one of the sun beds along 14th street.

There are cooling water fountains to deep your feet into in the summer months when the city is teaming hot and lots of seasonal activities like Tai Chi, Meditation or Star Gazing available. Many of them are free.

If you want to learn more about this super original and nice part of the city that feels miles away from the crowded and busy spaces of this ever-busy city, you can join a walking tour, like The Secret of the High Line for an extra dose of hipster.

My recommendation would be one of Context Travel insider tours of the High Line so one of the expert architecture and art specialist docents they have can share all about the origins and today’s life on the High Line. The High Line is my favourite part of Manhattan and a reason enough for me to visit the area. The views over the city and across the river are peaceful and a nice reminder that Manhattan is an island.

2. Piano in Washington Square


Pianist at Washington Square

Pianist at Washington Square

On Saturday mornings, wander around Washington Square for music performances and piano playing, live. Bring a book and a coffee and enjoy the beautiful show.

I thought this was a one off during my trips but it is actually a regular thing. Is there a better way to explore a city than people watching against the beautiful sound of a live piano?

3. Chelsea Market


Chelsea Market

Chelsea Market

Wander around this refurbished warehouse filled with alternative New York designer shops, clothes stores and lots of bars and restaurants. Come in the evening for a drink following a good dose of retail therapy.

If you are an art lover or connoisseur, you can join an expert and private behind-the-scenes tour of the art galleries in Chelsea, one of this district’s most relevant contribution, by the hands of the curators and art experts from Context Travel. I am a huge fan of their tours and have taken a few across the world, from the Vatican’s Sistine Chapel to Tokyo’s Asakusa. They have the best docents and experts, especially on things like art and architecture.


4. Tenement Museum


Tenement Museum

Tenement Museum

Located by the Williamsburg Bridge, the Tenement Museum provides an insight into the lives of the immigrants who arrived in the US in the 19th Century. New York was founded by all the immigrants who came from Europe at the time and who made the city what it is today. The Tenement Museum will give you a good insight into what went on in the city at the time. A variety of tours are on offer including some of the shops in the area.

You can obviously visit the Museum on your own but I highly recommend that you get a guide and learn more about the entire American Dream those immigrants were pursuing when they got off the ship with a private tour that includes visits to other relevant landmarks of the same era like a cruise to the Statue of Liberty, the Ellis Immigration Museum, the 9/11 Memorial and the many building in this part of New York City that remind us of its strong immigrant influence.

5. The Rubin Museum


The Rubin Museum

The Rubin Museum

The Rubin Museum is a hidden gem in New York City and the largest collection of Tibetan Art in the world. Come here for a guided tour or a self-guided one.

On Friday night, there is live music and free entry after 6pm, is there a better way to enjoy Friday night in the Big Apple?

Art from China, Nepal, Pakistan, India and Bhutan find a home under this Museum, but the focus is on Tibetan culture. Volunteer guides can be found around ready to provide details on the beautiful works on display. They are passionate and knowledgeable and are there simply to share their knowledge so it is very nice to be able to chat to them.

Here is my complete guide to Tibet if this exhibition ignites your interest.

6. A day in Williamsburg


Street Art in Williamsburg

Street Art in Williamsburg

An area dating back to the 17th Century Williamsburg, today, is the center of the New York hipster community. Entrepreneurs, artists and creatives are moving into Williamsburg and turning the area into a thriving, flowery and colourful part of the city.

Expect funky cafes, pop-up food markets, alternative New York designer shops and a melting pot of cultures as the previous residents of the area blend in with the new wave of gentrification. Spend the day at the flea market (on the weekend) and then wander around the main streets for second hand finds, great coffee, brunch, sex shops, record stores, parks (there is even a tiny stretch of beach facing Manhattan), Brooklyn Brewery tours (always with a queue), and all-round hipster New York life. You may want to catch an independent movie at Nitehawk Cinema top top the day off.

Wandering the streets is the best way to enjoy Williamsburg. If you also want to taste it, the food walking tours of the area are fantastic as they will take you to the small stores that are famous for having contestants from Master Chef and other programs alike. If you want to know what the next foodie craze may be, this is probably the place to see it first.

Although food is key to Williamsburg, Art is really what makes the neighbourhood so special, so make sure to join an expertly guided art tour to uncover the alternative art movement.

7. Union Square Greenmarket


Union Square greenmarket

Union Square greenmarket

A pretty market in one of the busiest parts of Mid-Town. Union Square is nice on its own but even better on the four days a week (Monday, Wednesday, Friday and Saturday) when the local farmer’s market, Greenmarket, is on. The stalls in operation every day will vary but the website has all the information including a handy map and even an app you can download to see what producers will be there every day. The site is also updated with severe weather changes.

Expect to buy organic and local food and, even if you are not in for grocery shopping, the general people-watching opportunities are always fun. Buy some food you can then take to Central Park for a picnic (see the other activities below for opportunities to eat your picnic)

8. Tea at The Plaza


Tea at The Plaza

Tea at The Plaza

The renovated Courtyard, a New York institution at New York’s most emblematic hotel, The Plaza, is the best place for a decadent tea and a dose of opulence. Have a cocktail, a premium luxury Grand Cuve tea and their fabulous scones, lemon curd and pastries. If you are looking for more affordable places to eat in the city, head out to Tales from a Fork.

Scroll down for more ideas of things to do in NYC

Click the image below for my full review of brunch at the Plaza

9. Boating in Central Park


Central Park

Central Park

Ok, so this may in fact be a touristy thing, and I know I promised not to tell you about those and to focus on the hipster things to do in New York City instead, but who can resist a romantic, cheesy boat ride along the lake? And I promote to give you some additional ways to make it special and different.

For the romantic take on the park an afternoon paddling along the lakes on Central Park is a regular of the city’s rom-com movie scenes. After all, the park is the most filmed location in the world with 305 movies with scenes shot on location including The Avengers, Wall Street, Date Night, Eat, Pray, Love, Bora, Night at the Museum, etc.

Do like Hollywood actors and actresses and pass time in the lush, green surroundings while you savour the goodies you bought at the market.

Enter through the Upper West Side and look for the lake. If you want to make a day out of it with an active take on the city (who would have said it is possible to have a day out in nature in new York City?), you can also rent a combo of a bike plus a one hour boat ride here.

Not keen on a boat but more on touring all of the park’s famous spots? You could feel like Carrie in Sex and the City and ride a horse drawn carriage, or you could join a Central Park pedicab tour and avoid the horse smell, the poop and get a side of humour and history thrown in for good measure. You can book one for as long or as short as you want and ask to be taken to the spots you want to visit and make stops for photo ops.

10. Times Square at sunrise


New York time square

New York time square

This is the city’s most visited sight and regularly tops list of the most visited landmark in the world so it is hardly a hipster part of New York. However, I will show you how to do it like nobody has done before.

New York only goes to sleep when the sun comes up. I know because in my jet-lagged body, I was up at 5am a number of occasions and found myself wandering the streets, looking for a place to see the sunrise. And at that time, there is a mix of party-goers coming home, drunken people and the earliest of the early risers. Plus some zombie-like tourists with jetlag like me.

Silly me, I thought the High Line would be open (it’s a park after all isn’t it?) so I headed there with the hope of seeing the sun come up against the river from its elevated position, only to find the gates closed. So I headed to Times Square.

At that time, the city looks like it has not yet gone to bed but as soon as the first sun rays come up the night life disappears and vampires return to their coffins. It is the only time of the day when Times Square will be empty and you can have it all to yourself, well worth the early start (or late finishing). A very alternative way to see New York City’s most famous landmark.

11Tango lessons

Every Saturday at 7,30pm there are tango lessons on Central Park. Tango aficionados gather from 6-9pm looking for a partner to practice.

Arrive, look for a partner and dance for four songs before swapping partner. Tango music plays in the background. If you are not brave enough to join in, watching is mesmerizing. The video above is proof.

 

 

12. Night Courts

Just like in the movies and on TV (and those who know me know I LOVE CSI), all the people you see sitting at the backbenchers in the Courts as cases are dealt are regular people.

Some are family members of those being tried others are the policemen escorting them. Anybody can go to the Night Courts and hear the judges pass decisions as the proceedings are public. A truly fascinating evening out watching the American justice system at play.

13. From Prohibition to Cocktail Hour


"Flatiron"

Flatiron


Where there are today Happy Hours there once was Prohibition. You can simply enjoy a drink at one of the many fashionable and awarded cocktail bars in New York City or join a sociologist or spirits journalist and explore the Prohibition era speakeasies and today’s cocktail culture.

Learn more about the ingredients, the bar that invented famous cocktails and the art of mixology from expert bartenders. After the tour, you can put everything you learned into practice and continue the night away in the Flatiron District.

14. Explore the skies in style


New York time helicopter

New York time helicopter

What more fashionable way to go to the airport than on an helicopter? You can hire a private helicopter to take you there instead of on a scenic tour, of have a bit of both. The best part about a helicopter airport transfer? There is no traffic in the skies so the one hour trip is cut down to just six minutes to the airport’s helipad.

Alternatively, if you have a lot of luggage or prefer to enjoy the scenic views, New York is a fabulous city to see from the sky and there are many ways in which you can do so, from the shorter and more affordable helicopters tours to the longer ones and even the night heli trips over Manhattan and the surroundings. There is even a photography tour which takes you to the skies without the doors! Talk about adrenaline rush.

15. Food tour of Harlem


Sylvia's in New York

Sylvia’s in New York

Harlem is a famous New York City borough that was a thriving African American writer and artist community at the turn of the 20th century. The area started off as a rural Dutch community and is best known for its troubled 60s and 70s. Today, it is one of New York City’s foodie paradise and an eminently proud and heritage rich part of Manhattan.

Almost every single cuisine is represented in one of the many neighbourhoods in New York but if you are looking for a tour with a dash of history and soul, join one of the walking Soul Food tours of Harlem. Expect buttery biscuits, waffles with bacon, prawns, eggs and fried chicken as representatives of the African and Caribbean cuisine that is famous of the area as you hear and understand more about Harlem’s past and rich history. I love coming to Harlem every time I am in New York and this tour is a great sample of what’s on offer so you can come back to discover the rest. If you want a more rounded experience, you can combine the food tour with a jazz session, the two go hand in hand in Harlem. Check the details here.

If you want to have a bit more of soulful experience in this upper side of Manhattan , you can also join a gospel tour on Sunday morning and let the music transport you and get under your skin.

16Apollo Theatre


New York Apollo

New York Apollo

Easy to combine this with the previous, Apollo Theater is one of the most famous landmarks in Harlem and it is steeped in history. First opened in 1914 as an all-white theater, it then closed and reopened in 1934 as a place to showcase African American talent. It was billed as the place where “Stars are born and legends are made”.

Although not unknown to tourists, the Apollo Theater receives 1,3 million visitors a year, it is a worthy visit to understand African American history and struggles. I strongly recommend you do so on a tour so that you understand what the walls can’t say.

The theater offers tours once or twice daily, depending on the day of the week, but you can add something extra special. There is a tour which includes multimedia representations in the main parts of Harlem followed by a tour of the Apollo Theater which ends with a mock of Amateur Night. Music and images are used at the main landmarks in the neighbourhood to explain the impact that music and art had on life in Harlem.

17. Daybreaker pre-work parties

 

Sunrise parties with Daybreaker

Sunrise parties with Daybreaker

It may sound crazy but New Yorkers know it best when it comes to working hard and playing hard. Forget getting drunk after work, letting yourself lose before going to the office is the new thing, sans alcohol, so you actually arrive fresh and reenergised, not groggy and exhausted.

Daybreaker organizes early morning parties, from 6am to 9am, where parti-goers let some steam off before heading to work in a healthy and pure environment. Put on your fancy gym clothes, your trainers, grab your coconut water and head to one of their venues for an early morning dance party to burn some calories in style. Dance like noone’s watching, because the idea is for the participants to encourage each other to be silly and let go.

Daybreaker parties happen across the globe but started here. You will have to check their schedule and location as these vary and have a pop-up component to them.

Where to stay in the Chelsea, Greenwich, Lower Manhattan Area

The Greenwich Hotel

Owned by Robert de Niro, this is a blend of East and West with art pieces spanning the globe, from Tibet to Morocco in bright colours. A touch of glam in New York’s most alternative neighbourhoods.

SoHo Grand

Industrial loft living matching the 70s style in this high ceiling, brick-walled hotel that is stylish and minimalistic.

Where to stay in the Mid Manhattan Area

W Hotel

All of the brand’s party feel at the heart of Times Square. This is the hotel that never sleeps. Fun, beautiful people, music and parties.

High Line

A more affordable, masculine and cozy hotel by the High Line which has a casual vibe, a hipster look and rooms that are homey and warm, with their own fireplaces, old books and vintage pieces, including the sink and the tables.

Knickerbocker

Housed in a Beaux-Arts building from 1906 that used to be a hotel, the staff wear the eponymous outfit and add a touch of freshness. The rooms are sober in muted colours and perfectly soundproofed so you see Times Square but not hear it.

NoMad

Its location, north of Madison Square, gave the NoMad its name. Inside, thick leather sofas, dimmed lights, thick velvet and strong drinks set the tone.

Baccarat

The most impressive part of the hotel is the lobby, which has a flamboyant entrance. Marvel at the 2,000 Harcourt glasses that are lit with LED lights sparkling day in and day out. This is a flash hotel with class, if that was ever possible, but modest in the rooms.

Gramercy Park

The hotel with the keys to New York’s only private park of the same name, the Gramercy Park offers a modern Renaissance vibe with red and blue and Louise XV chairs.

Where to stay near Central Park

The Surrey

A breath of fresh air, familiarity and simplicity can be expected at The Surrey which rewards the little ones with frog backpacks and parents with an in-room mixologist cart. Location is peaceful, rooms are elegant.

The Mark

Leaving a mark on guests thanks to its focus on wellness and that black and white blocked geometric lobby. The mark is popular with the fashionistas and has its own black and white pedi cabs to take guests around.

The Ritz-Carlton

The sprawling suites come equipped with a fantastic view of Central Park, so the location cannot be beat. Think marble-topped bathrooms, plush large beds and service with a smile.

Park Hyatt

One of the most luxuriously appointed and most over the top hotels in the city, the Park Hyatt occupies the first 25 floors of the One57 skyscraper. Inside, you can relax at the indoor pool while swimming to the underwater music, or let the staff pamper you.

The Mandarin Oriental

The brand with some of the most decadent, mind-reading service that could not bring anything less than perfection, elegance and a touch of the East to the Big Apple.

The Plaza

An institution and the most coveted hotel in Manhattan, The Plaza is right in front of Central Park, on Fifth Avenue, and oozes as much old-world charm and opulence as can be expected with grand chandeliers, generous use of gold and ornate floors, walls and ceilings.

Remember to Pin this post to your #NYC board.

17 Hipster Alternative Crazy Things to do in New York City Pin