Hysterical and Fun Events in NYC You Won’t Want to Miss

Let’s face it: The Big Apple Is basically the capital of all things entertaiing, and there is no shortage of fun events in NYC, no matter what time of year you visit. It’s home to some of the country’s best dining, it’s the headquarters of professional musical theater, and it’s the most fashionable town in America. So, it should come as no surprise that NYC is also the location of a host of wacky and fun events that really don’t happen anywhere else in the world. Some are hysterical, some are impressive, and some are just plain puzzling. However, if you choose to participate in one of these fun events in NYC, you’re sure to have an experience you’ll never forget. Here are some happening you just can’t miss.

The Most Hilarious, Weird and Fun Events in NYC

Below are some of the most beloved, weird, fun NYC traditions. If you’re visiting and want an authentic New York experience, consider participating in one or some of the events below.

NYC SantaCon

NYC SantaCon is a longstanding holiday tradition that often has non-participants scratching their heads and feeling puzzled. SantaCon is a charity benefit in which people dress up as Santa (in a red Santa suit and hat and all), or other Christmas characters (think: a gingerbread cookie, an elf, or even an ornament) and hop from bar to bar across the whole city. Many bars throughout the city participate, offering drinks to all of the debaucherous people who show up in their festive seasonal costumes. A special note: because the group of people participating in SantaCon tends to be particularly revelrous, a lot of bars will ban people dressed up as Santa on the day of the event. So, it’s best if you’re dressed up, to stick to where the group goes, or if you’re not with the group, to not dress up in a costume that day.

To participate in SantaCon, a donation is suggested, and each year the organization donates all of the proceeds to a specific charity. You can also simply follow SantaCon’s Twitter and follow along live to see which bar the group will be at (then join in). SantaCon takes place every year at the beginning of December, and this year it will happen on December 8.

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No Pants Subway Ride

The subway is inherently a fascinating place, filled with endless types of people from all walks of life (and from all over the world!) One day of the year, it gets even more interesting: the No Pants Subway Ride day. Each year, a group called Improv Everywhere hosts the No Pants Subway Ride, where people show up to ride the subway in no pants! (But wearing underwear). Everyone is invited to participate, and the group broadcasts details about how and where it will take place.
The basics look like this: there are seven places throughout the boroughs where people can meet. Groups are split up and sent into cars. Each group is assigned a specific stop at which they should take their pants off. Then, when the subway doors close and take off from that particular stop, the entire group should take off their pants.
The No Pants Subway Ride always causes laughter, confusion, and lots of unforgettable memories. People who are watching tend to take pictures, but people who are participating aren’t allowed to—since the point of the event is to keep a straight face and pretend like nothing weird is happening.

If you want to take part in the No Pants Subway Ride, pay attention to Improv Everywhere’s website and social media. The date changes every year, so the unsuspecting public is not clued in.

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Polar Plunge at Coney Island

NYC can get really cold in the winter. However, some people do the unexpected each year when it’s frigid out: They dive into the water off Coney Island at the start of each new year. The event, which happens each year on January 1, attracts people from all over the city and world, including those who are members of the hosting group: the Coney Island Polar Bear Club (a group devoted to winter swimming). People gather on the shores of Coney Island wearing whatever they want, be it a bathing suit, costume, or their regular clothes. Then, when prompted, they all run and take a dip in the frigid water. Friends and family members wait at the shore with dry clothes and towels to help them warm up.

The Polar Plunge is a charity fundraising event that gives money to local causes, like the Alliance for Coney Island and the New York Aquarium. The event’s attendance can vary depending on the weather. On the years that it’s below freezing outside, attendance dwindles, but on the 50-degree days, there are a lot of swimmers there. If you choose to participate, be ready to experience something brisk and chilling—but also an excellent and rousing way to start a brand-new year. Make sure you register in advance if you want to participate.

Christmas fun events in nyc

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Mermaid Parade

Another very unique and fun event in NYC that takes place at Coney Island is the Mermaid Parade. This beloved tradition occurs every year in the summer, and it celebrates the art of local artisans and designers. Participants design floats celebrating mermaids. Then, they march through Coney Island showing off their art and costumes, while playing honky-tonk music. Each year, the parade contains about 3,000 people. It is now in its 38th year, and it has become a beloved annual event in both Brooklyn and across the city. If you want to simply take in the wonder and beauty that is the Mermaid Parade, head down to Coney Island to watch it. You’ll be impressed by all the over-the-top costumes and the hard work that people put into creating a fantastical, mythical, mermaid-focused experience.

Coney Island Mermaid Parade fun events in nyc

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The Oddities Flea Market

When you think about visiting a flea market, you probably envision walking through a brightly lit, maybe industrial feeling space with tons of people who are showcasing everyday knick-knacks and trinkets. If you’re thinking that NYC’s Oddities Flea Market might be something like this, then think again. The Oddities Flea Market happens a couple of times throughout the year at the Brooklyn Bazaar in Greenpoint, Brooklyn. The flea market features strange and unusual objects, and it is curated by a couple, Ryan Matthew Cohn and Regina Cohn, who were longtime, avid fans of the “odd culture” scene of Brooklyn, which they realized was dying out because of gentrification.

At the oddities flea market, vendors showcase and sell things that are weird, morbid, bizarre, and dark. Think: medical ephemera, taxidermy, bones, original art, and more. There are three floors at the Oddities Flea Market, so there is usually an endless amount of strangeness to explore. The Oddities Flea Market welcomes back previous vendors every time, and it also welcomes new vendors who want to sell their goods. So, if you’re in town for multiple flea markets, make sure to go back: there will always be something new and weird to find there.

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Movies at Green-Wood Cemetery

One of the most beautiful cemeteries in all of New York City is Green-Wood Cemetery. It’s also one of the most historic, and it is the final resting home of famous figures like Jean-Michel Basquiat, Leonard Bernstein, and Horace Greeley. You can visit Green-Wood during the day to tour through the beautiful and stunning gravesites and landscaping. Located just south of Park Slope in Brooklyn, it is a very hilly cemetery, and it offers an unforgettable view of Manhattan below.
However, if you want to experience a very unique happening in Green-Wood Cemetery, go to the movie series held there each summer. Rooftop Films, a company that shows films to the public, hosts a movie screening series in the cemetery, so folks can bring their blankets and chairs weekly throughout the summer and take in showings of their favorite cemetery-appropriate films.

If you go to the films at Green-Wood Cemetery, expect to see movies like The Evil Dead. You can also go on a catacombs tour of the cemetery at night (on different nights than the films), if you really want to be spooked. Spending time at Green-Wood is a great way to get in some New York City history, to experience some thrills and chills, and to bask in the nice NYC summer weather.

fun events in nyc

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International Pillow Fight

Each year, thousands upon thousands of people in NYC gather in designated areas and have a pillow fight with each other. The pillow fight lasts for several hours. This may sound weird, but it’s real: it happens each year in early April on what is now called International Pillow Fight Day. The event takes place outdoors, in parks and squares. You can bring your own pillow, or take advantage of one provided by organizers. You can also wear a costume if the spirit moves you (but you don’t have to be wearing a costume to participate).

The locations of the pillow fight change each year, so check the event’s website to see where you can go fight with strangers (in a fluffy way) when you are there. Also, if you bring a new pillow to the fight, you can leave it with the organizers and they will accept it as a donation for a local homeless shelter. Consider going to the fight to blow off some steam. Not only will you feel good expelling energy by hitting someone with a pillow, but there’s also a good chance you’re going to end up cracking up, too.

fun events in nyc

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The Annual Halloween Parade at Tompkins Square Dog Run

Fun isn’t reserved for humans in New York. There are also fun events in NYC that are tailored for your pooch, as well. One of the most fun events in NYC for dogs is the annual dog parade that happens each year in Tompkins Square.
The parade happens around Halloween, and you can dress your dog up in his best costume, then take him to the park to show off (and hopefully win a prize!) The parade attracts a crowd each year, so if you are in town without your pet, don’t worry. You can still go down and enjoy the spectacle. If you do have a pet, there is no need to pre-register. Just show up and let your adorable dog do all the work for you.
In the middle of the event each year, there is a runway competition. Owners walk their dogs in costumes down a runway. Judges take in the outfits and performances, and then they pick a winner. There are other fun events for humans that take place at the dog parade, including raffles.

When you go to NYC, of course, you should look up the best restaurants, museums, and shows that you want to go to. However, you may also want to take a further peek into what fun events are happening that will have you chortling with laughter (and other people scratching their heads). By attending one of the experiences above, you can do something completely unforgettable, and you can return home to boast about your uniquely NYC experience.

ompkins Square Halloween Dog Parade

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