I spent 24 hours in Times Square — and had the time of my life

Aug 1, 2022

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If you ever mention Times Square to a New Yorker, they’ll wince and assure you that they never go there. That part of town is for tourists and giant, googly-eyed mascots. It’s crowded. It’s loud. It’s overwhelming. You’d have to be crazy to venture into that section of Midtown.

After living in New York for the summer, I was curious: Is Times Square really all that bad?

I set myself a challenge: spend 24 hours in Times Square fully embracing the tourist experience. 

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Traversing the busy streets of Times Square is not for the faint of heart. (Photo by Halle Newman/The Points Guy)

While I was excited to take on Times Square, I didn’t want to do it alone. So I invited my favorite travel buddy on my mission: my mom. We planned the trip together and set a few ground rules to guide our 24-hour experiment:

  • Lean into all things touristy — no New York snobbery allowed. Go for the gaudy.
  • Talk to strangers, whether it’s someone in a Spider-Man costume or a Floridian family (just to give some examples of people we met).
  • Stay out all day. No hotel breaks are allowed. Thus, be prepared: carry a water bottle and bring a sweater for indoor air-conditioning.

My mom and I are Vermonters — we’re used to mountains, not metropolises. We embraced our out-of-towner roots as we embarked on our 24-hour adventure.

The following is the story of our epic day — and night — immersed in Midtown madness. There are also a few tips, so you, too, can take on Times Square and — who knows? — maybe have the time of your life.

Arriving in Times Square

The subway is the best option for accessing Times Square if you are staying in any one of New York’s five boroughs, including Manhattan. If you’re already close by, walking also works.

To reach Times Square from outside of the city, though, commuter rail is your best friend. First-timers should definitely avoid driving in the actual city; the roads are crowded, drivers are aggressive and there are lots and lots (and lots!) of pedestrians to avoid.

Since my mom and I were coming from north of the city, we left our car in the town of Larchmont and hopped on a Metro-North train to Grand Central Terminal. While Westchester County, New York, is probably the only place New York City dwellers scoff at more than Times Square, it’s an excellent place to start your New York City adventure; our scenic 45-minute ride cost just $9.50 per person. If you’re coming in from the South or West, New Jersey transit would be the way to go.

After we’d marveled at Grand Central for a short while, we attempted our first real New York task: hailing a taxi. I felt like Carrie Bradshaw as I stepped to the curb and caught a cabbie’s attention. It would have been faster to walk to our hotel, but this adventure was all about tourist must-dos, so we sat through the gridlock and conversed over the cacophony of horns.

Do we get extra points for the size of our taxi? (Photo by Halle Newman/The Points Guy)

Related: Why I did a staycation in Times Square during the pandemic

Voco Times Square South

Times Square is a district rather than an actual “square.” Our hotel, which says it’s in Times Square South, was on 36th Street and 8th Avenue, so it’s a stretch. It’s sort of like how some shows are “off-Broadway” — some hotels are just “off Times Square.”

The voco is an IHG hotel that we booked with 50,000 IHG Rewards points, which TPG values at $250. Since cash rates were more than $300 per night (including service charges and tax), it was a good deal. With its chic bumblebee-yellow trim and modern feel, the hotel’s lobby gave off a chill, trendy vibe.

Our room had a generic, chain hotel feeling: neutral, functional — and compact. If you want a room with a view, you’re better off in a high-rise hotel closer to the nucleus of Times Square.

There was nothing exciting about our room or view, which was fine because we were out all day. (Photo by Halle Newman/The Points Guy)

Related: Wasting away again in Times Square: The new Margaritaville Resort is a slice of island paradise in an urban jungle

Broadway, baby

Experiencing a Broadway show — the best theater in the world — is a cardinal reason to brave the busy streets of Times Square. When you step inside one of Broadway’s ornate theaters, the chaos dissipates as the story unfolds and music emanates from the stage.

I used an app called “TodayTix” to reserve Broadway tickets. The app tells you which shows are running, the seats available and the cheapest prices.

“Hadestown,” a show that originated in my home state, had plenty of tickets available. I bought orchestra tickets for $99 each (it was worth every penny), but standing-room-only tickets cost as little as $39.

The Walter Kerr Theater has been home to “Hadestown” since 2019. (Photo by Halle Newman/The Points Guy)

As soon as you leave the respite of the theater, however, it hits you exactly where you are: the busiest block in town. I was initially overwhelmed, but soon found there was beauty in the chaos. All these people had spent their evening absorbing world-class theater, they had traveled far and wide and braved intense crowds to experience art.

Plus, there is no place better than Times Square at 10 p.m. to people watch.

Cocktail time

Sipping a cosmopolitan at St. Cloud. (Photo by Halle Newman/The Points Guy)

After the show, my mom and I headed up to the Knickerbocker Hotel’s rooftop bar, St. Cloud. The Knickerbocker is a classic luxury hotel built in 1906 by business magnate John Jacob Astor. During Prohibition, it was more than just a ritzy hotel: thirsty New Yorkers could sneak through an underground entrance by the 42nd Street subway station to access a secret bar.

Rumor has it that the Knickerbocker was the birthplace of the martini. John D Rockefeller is said to have named the drink after the bartender who made it for him (Martini di Arma di Taggia). These days, the Knickerbocker attracts more tourists than tycoons, but it still exudes Gilded Age glamor.

My mom and I sipped our cocktails under fairy lights and vines. We surprisingly didn’t have a view of the city — it wasn’t a brick wall situation as such, but it’s not a place to head for glorious New York panoramas. It was still fun to be on a rooftop, though, and my cosmopolitan certainly didn’t disappoint.

Related: Every tourist in New York City makes these 11 mistakes

New York pizza

The perfect New York picnic, courtesy of Carnegie Pizza. (Photo by Halle Newman/The Points Guy)

While Times Square has plenty of gourmet spots for foodies to nerd out, you just can’t beat New York pizza.

Carnegie Pizza is a tiny restaurant, located on 41st Street and Seventh Avenue, serving pizza slices for about $4 each, which is bougie for a city with 99-cent pizza on every corner. It was worth the splurge; this was the best pizza I’ve had in New York. The cheese was cooked to perfection atop the thin (but not too thin) crust, and the salty flavor mingled with the rich, sweet homemade dough.

Carnegie had a few indoor and outdoor tables — but even at 11 p.m. it was packed. We found a place to sit, close to Bryant Park, and watched the people around us play chess and chat as we enjoyed our late night picnic.

The joy of Times Square is simply taking in the scenes around you, whether you’re at a Broadway show or just watching passersby on the street.

Related: 8 songs that will make you want to visit NYC

Midnight moment

Every night from 11:57 p.m. to 12 a.m, the gargantuan billboards in Times Square synchronize to present the world’s largest digital art show. Midnight Moment features a different artist each month and anyone can apply for their artwork to be shown.

Even the famous New Year’s Eve ball lights up in synchrony with Midnight Moment. (Photo by Halle Newman/The Points Guy)

The featured design looked like a fuchsia Northern Lights of sorts. While the artistry was beautiful, the overall spectacle of Midnight Moment was not as compelling as I’d expected. Many of the billboards continued to run ads alongside the art, diluting the illusion of the display.

For me, what ended up being more interesting than Midnight Moment was a guy in a Spider-Man costume climbing up a walk sign pole.

Times Square is probably the only place in the world — besides Disneyland — where you’ll see six Spider-Men on the same block. (Photo by Halle Newman/The Points Guy)

In Times Square, much of the excitement is random and spontaneous. On our walk back to the hotel, we stopped to watch street performers front flip over audience volunteers.

Love it or loathe it, there’s never a dull moment in Times Square. (Photo by Halle Newman/The Points Guy)

Related: A beginner’s guide to New York City: Everything you need to know for your first trip

Ellen’s Stardust Diner

The next morning, we headed to perhaps the tawdriest place in Times Square: Ellen’s Stardust Diner. The diner isn’t your average mom-and-pop joint. It’s a musical diner where waitstaff sing show tunes while serving pancakes. Ellen’s Stardust Diner aims for waitstaff to go “from burgers to Broadway,” which many Stardust alumni have done. In 2019, 18 servers were cast in Broadway shows, one of which was — rather fittingly — “Waitress.”

A waitress belts “Wicked” to a captivated audience of diners. (Photo by Halle Newman/The Points Guy)

Since the diner is a huge tourist attraction, there was a line out the door to get in. Ellen’s Stardust Diner doesn’t take reservations, so expect to wait. At 10 a.m. on a Friday, though, we only waited about 10 minutes for a party of two. Standing in line is part of the Stardust experience. You can peer through the windows at performers and anticipate your turn inside.

To my surprise, the vibe in the diner didn’t feel as over-the-top ridiculous as I thought it would, once I gave myself over to the experience. Since all the customers had bought into this particular dining concept, everyone was supportive and enthusiastic. Customers applauded uproariously after each tune and many grinned in excitement when their party’s waiter got up to sing a song.

The food here was pretty bad, but you don’t come to Ellen’s for the cuisine; you come to hear hopeful stars-to-be sing their hearts out. I’d go back in a heartbeat.

Related: A love letter to New York City

The M&M megastore

Feared by many, faced by few, the iconic M&M store is located in the middle of Times Square. Here, you can buy M&Ms in bulk, but don’t mistake it for penny candy, it’s super expensive. There are fluorescent M&Ms and flavors frightening enough to leave taste buds in a state of utter despair. So, of course, I had to try the craziest ones. (The things we sacrifice for journalism….)

Once my mom and I collected dozens of different flavors and colors of M&Ms, we mixed them together in a bag and sampled them roulette-style. 

 

We killed a couple more hours sampling perfume in the Sephora store and browsing in Kinokuniya, a Japanese stationery and book store. Both of these stops were so much fun and offered an air-conditioned incentive for shopping.

The grand finale: Sardi’s

As our 24 hours drew to a close, my mom and I strolled over to Sardi’s, an upscale, old-school New York restaurant.

Sardi’s, which is almost 100 years old, is known for its walls lined with caricature drawings of Broadway celebrities. When a star visits the restaurant, they sign their autograph on their portrait. It almost felt wrong to enter the restaurant without a feather boa, a fur coat and stilettos.

While the restaurant was pretty much empty for our 2:30 p.m. reservation, I could feel the ghosts of vaudeville past as they drifted through the restaurant’s hallowed halls.

It’s not every day Barbara Streisand watches over you as you eat a chef’s salad. (Photo by Halle Newman/The Points Guy)

Sardi’s was a must for my mom and me to visit. As a kid, I was obsessed with the movie “The Muppets Take Manhattan,” which has a scene filmed at Sardi’s.

Years back, my mom had found a DVD of the “Muppets Take Manhattan” as a prize in the bottom of a cereal box. Now here we were, sitting where Kermit the Frog had once sat. In the empty restaurant, we reminisced happily about all the movies we’d seen that took place in the heart of New York.

Related: 9 of the best movies set in New York City

Takeaways

Times Square in times:

  • Times we heard Alicia Keys’ “Empire State of Mind” playing: four.
  • Times we used the compass app to navigate: four.
  • Times we got lost anyway: too many to count.

Spending 24 hours in Times Square made me stop and marvel at the stuff I usually walk right by or avoid altogether. I stopped trying to speed past slow-walking tourists; instead, I walked slowly alongside them, watching them take in the city.

Times Square is unapologetically loud, crowded and overwhelming. Yet millions of people still travel from all over the world to experience it — and they love it — because there’s nowhere else on Earth quite like it. Who cares if it’s not the trendiest, coolest place in the city?

Embracing Times Square. (Photo by Karen Newman)

Bottom line

My Times Square experiment baffled friends and family, but I had a fantastic time. My stay in this iconic area was so enjoyable that it ranks as a highlight of my summer. In fact, it changed the way I look at New York City.

Times Square isn’t about shopping, museums, gorgeous scenery, refined restaurants or other destination highlights. Times Square is about experiencing the beating heart of New York. It’s the physical sensation of feeling at the center of the city. It’s about standing on a block that people have written thousands of songs, movies, plays and stories about. You go to Times Square simply to be there

When you surrender yourself to the experience, you’ll discover something fun and magical.

Life is too short to miss out on Times Square.

Featured image by Siegfried Layda/Getty Images.

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