20 Things to Do in New York City in Your Twenties

Staten Island Ferry | InSapphoWeTrust/WikiCommons
Staten Island Ferry | InSapphoWeTrust/WikiCommons
The city that never sleeps is best enjoyed when one night of missed sleep won’t ruin you for the rest of the month. If you’re brand new to New York City, have been living here for a few years or grew up knowing every single neighborhood, there are certain things that are best enjoyed before you hit 30. Whether it’s bar-hopping to find the latest and greatest things around the city or finally checking those touristy items off of your bucket list, here are the 20 things you should make sure you do while you’re still in your 20s.

Discover your favorite rooftop bar

There is only one reason that all New Yorkers love summer and that is the opening of rooftop bars. Whether you’re into the midtown bars where you’re smack-bang in the middle of all the skyscrapers, the downtown roofs that give you some perspective or the bars along the waterfront in Brooklyn and Queens, everybody’s got their own personal favorite. We’re preferential to the city escape at Gallow Green, but spend your 20s hopping around to discover your own summertime rooftop vibe.

Venture further out

As a young New Yorker, you should have the energy to jump on the train and head beyond your comfort zone. Go to Queens to try authentic Tibetan food at Lhasa Fast Food in Jackson Heights or venture up to the lesser-visited Little Italy on Arthur Avenue in the Bronx. You’ll be able to bounce back if you miss a couple hours of sleep.

Spend a day on a blanket in Prospect Park

In the summer, everybody and their mother piles onto the Great Lawn in Central Park. Spend your 20s getting to know the park’s lesser-visited (but equally gorgeous) little brother, Prospect Park. Go armed with a cooler of beers, blankets and a frisbee and you may never go back to Central Park again. Just kidding. Maybe.

Go gallery hopping for free booze

Thursday nights in Chelsea are the best nights for art-loving people on a budget. Search all the gallery openings happening that night and plot out your course. Not only will you rub shoulders with some of New York’s coolest people, you’ll spend way less than you ever would on a Thursday at the bar. Find most openings between 21st and 27th streets between 10th and 11th avenues.

Check out the flea markets

One man’s trash is another man’s treasure. And for those who need proof that the age-old cliche is absolutely true, head to one of New York’s many flea markets at the weekend. We’re partial to Brooklyn Flea for not only its fun goods, but the food vendors who also set up shop every weekend.

Make reservations for a bottomless brunch

Cafe, American
Although most New Yorkers roll out of bed on Sunday and head to whichever brunch place has the shortest wait time, everybody should make a reservation at least oncefor brunch. Go to bed early the night before, set your alarm and then breeze past everybody waiting three hours or more for eggs benedict. Miss Lily’s not only takes reservations, but you can get unlimited drinks and an entree for $35.
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Eat your way through Smorgasburg

Food Stand, Market, Food Court, Food Stall, Farmers' Market, Philippine
Smorgasburg | Saaleha Bamjee/Flickr

It’s a well-known fact that your metabolism slows down the older you get. Take advantage of the fact that you can still eat vast amounts of food by doing a culinary tour of Smorgaburg. Beers, pasta, kimchi, fries, droplets of water … all is fair game at New York City’s most popular food market.

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Find your favorite beach and stake your claim

Natural Feature
Jacob Riis Beach
Jacob Riis Beach | David Shankbone/WikiCommons
Whether you’re preferential to Coney Island, the Rockaways or Jones Beach, start early each summer and claim your spot on the sand. Get there early, bring a book and make sure everybody knows that those few square feet of beach are reserved for you and your friends.
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Take an architecture tour

New York City is home to some of the world’s most fantastic and unique buildings. Get to know the history behind the buildings (and a bit of city history itself) on a walking tour to some of Manhattan’s coolest architecture. Then afterwards make a stop at the Center for Architecture to learn more about some of the city’s disappearing buildings.
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Board a ferry and cruise around Manhattan

Staten Island Ferry
Staten Island Ferry | Staten Island Ferry
New Yorkers don’t often take advantage of the rivers surrounding Manhattan. City dwellers who want to be on the water have quite a few options. You can take a ferry to Williamsburg, straight to IKEA or to the Statue of Liberty. But here’s one pro tip: The Staten Island Ferry is free and they sell beers onboard for less than $5. It’s the ultimate in cheap booze cruise.
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Go to a party at a warehouse in Bushwick

Spend the weekends of your early 20s keeping the party going strong well into the morning. Sorry to spoil your fun, but we can’t tell you where these parties happen. Although we will give you one tip: Bushwick is famous for its after-hours but you aren’t going to meet anyone in Manhattan who will lead you there. When the clock strikes 2 a.m., make sure you’re close to where you want to be around 7 a.m. Bossa Nova Civic Club is generally a good bet.
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Befriend somebody with a house in the Hamptons

Montauk Point Lighthouse
Montauk Point Lighthouse | Montauk Point Lighthouse
By the time you reach 29 there is only one thing that EVERY New Yorker must do: befriend someone with a house outside of New York. Start working on this project in the dead of winter so they won’t suspect your true motives. You’ll probably meet them at a posh event, so save up your dollars and go to one of Manhattan’s coolest bars—try starting at The Bar Room at The Beekman Hotel—in the middle of the week.
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Go to an arthouse movie screening in the village

Every New Yorker gets moody once in awhile. If you just need a couple hours away from your life, duck into one of the arthouse cinemas in Greenwich (we personally love Film Forum.) Plus, they’re usually a lot cheaper and less crowded than the movie theaters playing the latest releases.
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Go to that comedy show your friend of a friend is in

Bar, American
If you don’t know somebody in New York that’s on a comedy or improv team, there is a 100% chance that one of your friends does. And you will, inevitably, be asked to attend one of their shows—probably at the Upright Citizens Brigade. It may be hysterical or it may be awful, but every 20-something New Yorker should have to sit through the spectacle of people on a stage trying to make you laugh. It builds empathy.
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Cheer on your favorite baseball team

Yankees | Yankees
Mets or Yankees? Whatever your preference, make a plan to go to at least one ball game over the summer. Although fair warning: Concessions may get a bit pricey. We’re not telling you to sneak beers inside, we’re just telling you that if you get away with it, you’re going to have a fun game.
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Wait in the cold for the Macy's Thanksgiving Day Parade

You are not going to want to do this in your 30s. It’s cold and it’s full of tourists and you have to stand in one place for hours. If you’re stranded in New York City for Thanksgiving without your family, make the best of the situation and head to midtown to watch the fantastic Macy’s Thanksgiving Day Parade. C’mon, you know you always dreamed of it when you were little.
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Row your boat in Central Park

You may think it’s something solely reserved for tourists, but everybody should go rowing on the Central Park lake at least once in their lives. Head out with a group of friends to make some memories or save the occasion for that one Tinder date you actually kind of really connected with.

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These recommendations were updated on June 27, 2019 to keep your travel plans fresh.