What Iconic Holiday Movie Destinations in NYC Look Like in Real Life

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.

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.”


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


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 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

Gabbi Shaw/Insider

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.”


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



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



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



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.

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.

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.”


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.

Here are the two main characters enjoying their Frrrozen Hot Chocolate.




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.

In “Scrooged,” a modern re-telling of “A Christmas Carol,” Bill Murray’s character works at the Seagram Building.




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.

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