What makes shopping on 5th Avenue so iconic?

Once plainly designated as “Middle Road” in the 18th century, 5th Avenue has come a long way from connecting unsellable vacant lots and cattle farms. Along came the Vanderbilts and subsequent mansions in the 19th century to launch what is known today as one of the most exclusive shopping streets in the world.

Even if you’re not a descendant of New York Gilded Age railroad tycoons, shopping on 5th Avenue has that certain je ne sais quois. Stretching over 135 blocks north-south in Manhattan, here’s your guide why 5th Avenue is just so iconic — even if you’re just window shopping.

The famous shops

What’s in a name? Turns out, quite a lot. Louis Vuitton, Cartier, Gucci, Bergdorf Goodman… all the high label fashion icons call 5th Avenue home. There’s even its own namesake department store, Saks 5th Avenue, which is a travel destination all its own. Tourists and locals alike make their pilgrimage every winter season to take in the wonder of their holiday window decorations.

But it’s not only the gilded names that have an address here. Nike’s House of Innovation 000 and Apple’s NY flagship store are some of the newer residents that round out the legendary shopping experience.

The serene parks

You may notice that 5th Avenue doesn’t have a lot of the famous NYC stoops. That’s by design: the city ordered the removal of stoops and truncating sidewalks and mansions along 5th Avenue in the early 20th century. The reason? To widen the roads for automobile traffic.

But that doesn’t mean you won’t see patches of green. Lucious parks line the avenue between shopping stops. Maybe you’ve heard of a little place called Central Park? 5th Avenue’s delta, however, is in lower Manhattan. Greenwich Village’s Washington Square Park is block #1 of 5th Avenue.

Traveling north from there, you can take rest stops at many more historic parks: Madison Square Park, Bryant Park, and Marcus Garvey Park in the Bronx are all along Fifth Avenue. They’re the perfect spots for people-watching, semi-forest-bathing, and taking a break from schlepping shopping bags.

The standout landmark buildings

If you need a break from looking for deals, look up. This avenue connects buildings that help make the Manhattan skyline what it is. Walk (or come up for air from the 4/5/6 train) and take in the splendor of The Flatiron Building on 23rd Street. Then keep heading north to crane your neck at the Empire State Building off 34th. After stopping into The Travel Agency — Fifth Avenue, cast your gaze on Rockefeller Center at 49th.

But it’s not just sky-high architecture that rules the facades of 5th Avenue. St. Patrick’s Cathedral may not rise above the rest physically, but it’s still a grand example of Gothic Revival architecture. Even if you’re not religious, the sights and sounds of the cathedral aren’t to be missed. The church has two organs, each with more than 9,000 pipes, and its 94 stained glass windows sparkle in the sun. The only bad news is that your phone camera and mic won’t be able to capture them accurately, so fully enjoy them IRL.

The impactful, world-famous museums

For a street called “Museum Mile,” you’d expect nothing less than a long list of historic museums along the way. The most famous museum stops on 5th Avenue include The Metropolitan Museum of Art (or for short, The Met), the MoMA, and The Guggenheim. But be sure to also consider the Cooper Hewitt Smithsonian Design Museum and Museum of the City of New York worthwhile stops on your cultural journey.

The blockbuster movie appearances

New York City has long been a stage for famous movies, but 5th Avenue is one of the most frequent leading actors on the call sheet.

Let’s start with arguably the most recognizable 5th Avenue film, the 1961 rom-com Breakfast at Tiffany’s. The movie opens with Audrey Hepburn getting out of a cab right outside the jeweler’s flagship store, paper bag breakfast in hand. Ghostbusters, The Thomas Crown Affair, Spider-Man,John Wick, and many others have used the New York Public Library off 5th Avenue as a turnpoint location. In the feel-good film Taxi Driver, Robert De Niro as a cabbie heads to 5th Avenue and 55th Street to pick up his final fare at the St. Regis Hotel.

The list of 5th Avenue movies is endless, but no list is complete without two words: King Kong. Many miniature props (and in modern days, CGI) were used to recreate the Empire State Building and Midtown Manhattan. Even if it wasn’t shot on location, King Kong underlines just how iconic, famous, and historic 5th Avenue really is.

See you on 5th Avenue, and at The Travel Agency — Fifth Avenue

We might be a bit biased about this one, but we can’t leave our favorite shop off the list. The Travel Agency opened its third location on Fifth Avenue in May 2024, a couple of blocks away from Radio City Music Hall. With Grand Central right down the road, it also means that our Fifth Avenue shop is an easy travel destination — and a jumping-off point of sorts. They say it’s all about the company you keep, and we’re feeling right at home.