I visited some of the most iconic holiday movie locations in New York City and have never felt more cheer

30 rock christmas tree and ice skating rink
The tree at Rockefeller Center. Gabbi Shaw/Insider
  • New York City is one of the most popular settings of holiday films and TV shows.
  • I visited locations from “Miracle on 34th Street,” “Elf,” and others to see what they’re like in real life.
  • It was a day filled with Christmas cheer, NYC magic, and very long lines.

As soon as Santa rides in on his sleigh during the Macy’s Thanksgiving Day Parade, it feels like New York City becomes a winter wonderland almost overnight.
30 rock christmas tree
People photograph the Christmas tree in Rockefeller Center before sunrise on December 5, 2019, in New York City. Gary Hershorn/Getty Images
There’s already so much to do and see in New York City on a normal day, but the holiday season adds another festive layer to the city. It’s easily one of my favorite times of year to walk around in Manhattan.
And with all that magic, it’s no wonder that so many writers choose to set their holiday films and shows here.
Home Alone 2
‘Home Alone 2.’ 20th Century Fox
To name a few, there’s “Elf,” “Home Alone 2: Lost in New York,” “Serendipity,” “Dash + Lily,” “Scrooged,” and even Disney+’s latest Marvel series, “Hawkeye.”
I mapped out a route from Union Square to Midtown so I could visit as many holiday movie locations as possible. This is the route I took.
My route
My route. Google Maps
I started at the Union Square Holiday Market, then headed downtown to the iconic Strand Book Store. Then I hopped back on the subway and arrived at Macy’s flagship store on 34th Street at Herald Square.

From there, I stayed on Fifth Avenue and walked uptown, stopping at Rockefeller Center to see the Christmas tree and the ice-skating rink, the Plaza Hotel, and the Wollman Rink in Central Park.

Then I headed into the Upper East Side to see the famous Serendipity 3 dessert spot. To cap off my journey, I went back downtown to visit the Seagram Building on Park Avenue. My day was done, after many stops, lots of Christmas music, and 18,395 steps.

My first stop was the holiday market in Union Square. Recently, it was featured as a location in the sweet Netflix series “Dash & Lily.”
Union square holiday market
The Union Square Holiday Market. Gabbi Shaw/Insider
This year’s market features over 160 vendors and is open until Christmas Eve.

Something I appreciate about the Union Square subway stop is that, if you can figure out how to navigate it, you can climb up the stairs directly into the market.

The market is kind of like a maze — it’s here where Dash and Lily almost run into each other for the first time. I can see how the two miss each other.
Union square holiday market
The holiday market. Gabbi Shaw/Insider
Especially if the market had been more crowded, like in the pre-pandemic days, I don’t know how anyone would be able to find anyone else.
Here’s what it looks like in the show.
Union square in dash and lily
‘Dash & Lily.’ Netflix
In the show, Lily is caroling with her friends while Dash is just trying to get out of the market without thinking too much about his ex.

Unfortunately, there were no carolers when I visited, but I did secure a hot chocolate to keep me warm on my journey.

Next up was another location from “Dash & Lily,” and an important one at that. It’s the place where Lily leaves her red notebook for Dash to find.
The strand
The Strand. Gabbi Shaw/Insider
The show, which is based on a YA novel called “Dash and Lily’s Book of Dares” written by David Levithan and Rachel Cohn, dropped on Netflix last winter.

It follows two diametrically opposed teenagers — Dash hates the holiday season (in fact, he calls it “detestable”), while Lily is all-Christmas, all the time. Lily’s brother convinces her to leave a notebook in the bookshelves of the Strand, hoping for the right guy to pick it up … which, of course, Dash does.

The two bond over doing different NYC-related dares via the notebook. One of the biggest scenes in the finale also takes place in the Strand, on New Year’s Eve. Highly recommend: It was one of my most comforting 2020 watches.

Here’s the inside of the Strand, which is on Broadway between 12th and 13th Street, just south of Union Square.
The strand book store
The Strand. Gabbi Shaw/Insider
The Strand Book Store is one of the most famous book stores in New York City. It’s been open since 1927 and famously has 18 miles (29km) of books inside.

If you happen to love book stores like I do, it doesn’t matter what time of year it is — the Strand will always have a bit of magic. But when it’s all decked out for the holidays, it’s perfect.

Here are some of the shelves in the aisles …
The strand
You could easily spend hours just combing the shelves for a special red notebook.
… like the one Lily leaves her notebook in.
Dash and lily the strand
‘Dash & Lily.’ Netflix
Of course, the real Strand does not have this same cozy, warm lighting. It also would never be this empty, as it’s a huge tourist destination.
My next stop was the Macy’s flagship store on 34th Street, the site of many holiday films including, of course, “Miracle on 34th Street.”
Macy's 34th street
Macy’s. Gabbi Shaw/Insider
The flagship store has 1.25 million square feet of retail space and a whopping eight floors, making it the biggest department store in the world.

The “Believe” sign is a reference to “Miracle on 34th Street,” as the plot of the film revolves around proving that the Macy’s Santa Claus is, in fact, the real Santa.

This is what it looked like in the 1947 version of the movie.
Macy's in miracle on 34th street
‘Miracle on 34th Street.’ 20th Century Fox
Macy’s doesn’t use this logo anymore.
The inside of Macy’s is decorated throughout.
Macy's 34th street
Macy’s. Gabbi Shaw/Insider
Overall, my time in Macy’s was festive but very crowded. I had to get off the first floor as soon as possible, or I would’ve been sprayed with at least five different perfumes.

Notably, when I got past the first two or three floors of Macy’s, the escalators switched to old-fashioned wooden ones, which helped me feel like I was going back in time to the era of the ’40s film.

On the top floor of Macy’s is where the famed SantaLand is. I couldn’t get in to see the actual Santa without reserving a ticket, but this is what the outside looks like.
Macy's 34th street
SantaLand. Gabbi Shaw/Insider
I heard the “elves” telling some kids that they grow smaller as they get older to explain why they’re larger than the elves at the North Pole, and that they only speak Elf, but learned English just for the holidays.

You can make reservations to see Santa here.

SantaLand has nods to its iconic beginnings, including a poster for the original 1947 “Miracle on 34th Street.”
Macy's 34th street
The poster. Gabbi Shaw/Insider
The movie was remade in 1994 starring Elizabeth Perkins, Mara Wilson, Dylan McDermott, and the late, great Richard Attenborough as Kris Kringle. 
SantaLand also has windows — just like store does outside — but theirs depict moments from the movie.
Macy's 34th street
A scene from ‘Miracle on 34th Street.’ Gabbi Shaw/Insider
The Macy’s holiday lights are legendary.
Walking out of Herald Square, I saw my next destination: the Empire State Building, seen in “Elf,” “Sleepless in Seattle” (to me, a holiday classic), and “Home Alone 2.”
Empire state building
The Empire State Building. Gabbi Shaw/Insider
I’ve lived in New York my whole life, and I’ve still never stepped foot inside.
The Observatory line was long, and it costs $US42 ($AU60) to get up there … so I settled for the view of the line.
Empire state building
The line for the Observatory. Gabbi Shaw/Insider
The revolving doors Buddy spins through over and over again are around the block on 33rd Street.

Turns out, the best way to look at the Empire State Building is from a few blocks away.

Here’s the lobby of the Empire State Building as seen in “Elf.”
Elf empire state building
‘Elf.’ New Line Cinema
In “Elf,” Buddy — a human who thinks he’s an elf — meets his real father, Walter Hobbs. Walter works inside the Empire State Building at a publishing company. There’s a memorable scene when Buddy pushes all the buttons on the elevator, making it look like a lit-up Christmas tree.
As I continued on my journey, I passed the New York Public Library — fittingly, the lion statues out front were adorned in their holiday best.
The lions at the NYPL
One of the New York Public Library lions. Gabbi Shaw/Insider
The statues were named Patience and Fortitude (seen here) by Mayor Fiorello LaGuardia back in the ’30s. Each year, they rock a holly wreath during the holiday season.
I also passed Saks Fifth Avenue, which has holiday windows that rival Macy’s.
Saks 5th ave
Saks Fifth Avenue. Gabbi Shaw/Insider
The Saks Fifth Avenue is on (of course) Fifth Avenue, between 49th and 50th Street — conveniently, it’s right across the street from my next stop, 30 Rock.
The Christmas tree at Rockefeller Center and its accompanying ice-skating rink have been featured in multiple movies and TV shows.
30 rock christmas tree and ice skating rink
The tree at Rockefeller Center. Gabbi Shaw/Insider
The first tree was erected at Rockefeller Center 90 years ago, in 1931. This year’s tree is a 79-foot (24.08m) Norway spruce from Elkton, Maryland.

I happened to get there right as the ice was getting cleaned, so I snagged a picture of the pristine ice-skating rink, which made it easy to spot the snowflakes being projected on to the rink.

Here’s Kevin visiting the tree in “Home Alone 2.”
Kevin in home alone 2
‘Home Alone 2.’ 20th Century Fox
Kevin’s love for Christmas trees is how his family is able to find him, but I can’t imagine being able to find anyone in that sea of people.
Buddy and Jovie in “Elf” have their first kiss at the ice-skating rink, too.
Elf
‘Elf.’ New Line Cinema
It’s after Jovie takes him to see “the big one” — aka the Christmas tree.
I had to snag a selfie with the tree before I left.
Me and the 30 rock tree
No tree visit is complete without a selfie. Gabbi Shaw/Insider
I kept my mask on because the plaza was a zoo.

An upcoming episode of “Hawkeye” will also take place here, as seen in the trailers.

The new FAO Schwartz location is next to the tree now. A toy soldier was making sure the store didn’t get too over-crowded.
Fao schwartz
FAO Schwartz. Gabbi Shaw/Insider
The iconic toy store used to have a giant store at 745 Fifth Avenue — everyone remembers the floor piano scene from “Big,” right? — but it closed in 2015. The building now houses a Bergdorf Goodman.

FAO Schwarz’s new location at 30 Rock opened in November 2018, where it remains to this day.

This whole area of NYC is completely decked out for the holidays — even the bus stops are decorated, and you can’t go more than 10 feet (3.05m) without hearing Salvation Army volunteers blasting music.
A holiday bus stop
A holiday bus stop. Gabbi Shaw/Insider
It’s impossible to be a Scrooge when the streets look like that.
Each store has its own take on decorating.
Chanel store
Another store on Fifth Avenue. Gabbi Shaw/Insider
This store is lit up to look like a wrapped present.
Before I knew it, I’d reached the Pulitzer Fountain on the edge of Central Park. It’s been transformed to an Arctic ice-skating rink with penguins and polar bears.
Central park fountain
The Pulitzer Fountain. Gabbi Shaw/Insider
It took 5,000 feet (1,524.00m) of lights and handmade icebergs and sculptures to complete the transformation of the Pulitzer Fountain, which was built in 1916 and is across the street from one of the most famous hotels in NYC …
To my left was the Plaza Hotel, which is looking a little less glamorous than usual due to scaffolding and construction.
The plaza hotel
The Plaza Hotel. Gabbi Shaw/Insider
The Plaza opened in 1907 and is one of the most famous (and expensive) hotels in the world — besides its legendary appearance in “Home Alone 2,” the Plaza has also been part of “Bride Wars,” “Eloise at the Plaza,” “Funny Girl,” and “Sleepless in Seattle,” to name a few.
Much of the hotel is off-limits for tourists, but the decorated lobby is open for all to look at.
The plaza hotel
The Plaza’s lobby. Gabbi Shaw/Insider
It was decorated beautifully.
The Palm Court is right off the entrance — it was decorated as well, and filled with guests.
The plaza hotel
The Palm Room. Gabbi Shaw/Insider
The Palm Court is where the Plaza holds afternoon tea.
Memorably, Kevin stays at the Plaza when he’s lost in New York — and he gets directions from future president Donald Trump.
Home Alone 2 Trump
‘Home Alone 2.’ Screengrab
At the time, Trump owned the hotel and, as director Chris Columbus told Insider’s Jason Guerrasio, “bullied” his way into the film. 

“We paid the fee, but he also said, ‘The only way you can use the Plaza is if I’m in the movie,'” Columbus said. “So we agreed to put him in the movie.”

In the end, Kevin asks Trump for directions on how to get to the hotel lobby.

I snapped another (subtle) selfie with the decor and then was on my merry way.
The plaza hotel
Never felt more out of place. Gabbi Shaw/Insider
Again, the Plaza is another New York landmark that I’ve never been to. One day, I’ll make it back for tea.
Although it’s the holiday season, it sure did look like fall in Central Park.
Central park
The bridge. Gabbi Shaw/Insider
Sure, this bridge is also part of the ending of “Home Alone 2,” but it’s also iconically in “The Devil Wears Prada,” a personal classic.

On this visit, I watched someone get engaged at the very spot I took this picture in, while I was standing on the bridge.

I continued walking north until I hit the Wollman Rink, a location featured in “Serendipity,” “When Harry Met Sally,” and “Gossip Girl,” among others.
Central park ice skating rink
Wollman Rink. Gabbi Shaw/Insider
Wollman Rink first opened in 1950 before closing from 1980 to 1986 for renovations. Until 2021, it was operated by the Trump Organization until Mayor Bill de Blasio severed ties with the company.
It looked a bit different back in 2001, as seen in “Serendipity.”
Serendipity ice skating rink
‘Serendipity.’ Miramax Films
It was rounder 20 years ago, and it doesn’t have the lit-up trees surrounding it anymore.
The way the rink appears in the season one holiday episode of “Gossip Girl” is closer to how it looks today.
Gossip girl ice skating rink
‘Gossip Girl.’ The CW
Blair Waldorf, played by Leighton Meester, is skating around Wollman Rink in the episode “Roman Holiday,” along with her father and his new boyfriend.
I walked by Bloomingdale’s, which was lit up for the holidays. It also played a role in “Serendipity.”
Bloomingdales on 5th ave
Bloomingdale’s. Gabbi Shaw/Insider
“Serendipity” is a 2001 rom-com starring John Cusack and Kate Beckinsale as two strangers who meet by coincidence and then decide that, if it’s fate, they’ll run into each other again.
But I had to finish out my mini-“Serendipity” tour with the place that gave it its name: Serendipity 3.
Serendipity 3
Serendipity 3. Gabbi Shaw/Insider
Serendipity opened in the ’50s and was popularized by stars like Marilyn Monroe and Andy Warhol.

The spot’s most famous drink is the Frrrozen Hot Chocolate, which is exactly what it sounds like. The recipe is now available on their website, but it was a closely guarded secret for years. Not even Jackie O could get her hands on it.

 

Here are the two main characters enjoying their Frrrozen Hot Chocolate.
Serendipity
‘Serendipity.’ Miramax Films
As Insider previously reported, Serendipity is very popular with tourists, though Insider’s Joey Hadden said she’d return for the frozen hot chocolate.
I had every intention of waiting in line for the dessert hot spot … but it would’ve taken over an hour.
Serendipity 3 line
The line outside Serendipity 3. Gabbi Shaw/Insider
From what I could tell, the inside looked very cozy and very pink.
My final stop on the tour was the Seagram Building from “Scrooged.”
Seagram building from scrooged
The Seagram Building. Gabbi Shaw/Insider
Built in 1958, the Seagram Building is a landmark of the NYC skyline and has won multiple awards.
In “Scrooged,” a modern re-telling of “A Christmas Carol,” Bill Murray’s character works at the Seagram Building.
Scrooged
‘Scrooged.’ Paramount Pictures
It essentially looks the exact same — the trees on the side of the plaza are just lit up for the holiday season.

As “Scrooged” isn’t the most traditional holiday film, it felt fitting to end my tour here, before I got Christmas-ed out.

As I started my walk back to the subway, I came across this fully decorated restaurant. Even though it’s not a famous movie destination, it proved that the holiday spirit is all around us — you just have to look.
A random restaurant in manhattan
A restaurant. Gabbi Shaw/Insider
I’ve never felt more Christmas spirit than how I felt after this walking tour of NYC, and I got to see some iconic destinations that I’ve never gotten around to visiting.

Now, it’s time for my Christmas movie marathon to begin.