Everything You Need to See on a Typical Stroll Along New York’s 5th Avenue

One of the world’s most famous shopping streets happens to pass plenty of New York icons and a few hidden gems.


An aerial shot of a long street running through a big city

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5th Avenue is synonymous with the wealth and extravagance that goes hand-in-hand with Manhattans shiny reputation. Known for its super high-end stores, restaurants and appearances in everything from Friends to the Devil Wears Prada, 5th is arguably New York City’s most famous thoroughfare.

It also makes for an excellent way to visit some of New York’s most iconic spots without the need for a map. With the avenue running in a straight line from the banks of the Harlem River all the way to Greenwich Village, you can get those steps in while seeing more than enough of NYC in a matter of hours.

We’ll start our hypothetical stroll under the Washington Square Arch, but you can of course go from top to bottom. So let’s get going!

Washington Square Park

The Washington Square Arch in New York City on a sunny day

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Greenwich Village’s famous green space began life as a tobacco field before being transformed into a military parade ground by the fantastically-named Alderman Abraham Valentine in 1826. 14 years later, and by then surrounded by some of burgeoning New York’s most desirable houses, the parade ground became a park with paths and greens installed.

In 1889, the park’s centrepiece, the iconic Washington Square Arch, was installed to commemorate the centennial of President George Washington, the park and arch’s namesake.

Today you’ll find street entertainers, yoga enthusiasts, joggers and even poets taking up every inch of grass on sunny days, so complete a circuit of the park before heading Northeastward to our next stop on 5th Avenue.

Flatiron Building

New York's Flatiron building with pedestrians and cars in front of it

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Around 20 minutes’ walk (or 8 minute taxi ride if that works better for you) you’ll encounter you’re must-visit New York icon – no, not the Harry Potter New York store around the corner, but the world-famous Flatiron Building.

The triangular skyscraper caused a stir upon opening in 1902, with New Yorkers expressing concern over the winds caused by the knife-edge pointing up 5th and Broadway, or generally mocking the unusual shape. However, the Flatiron Building has grown on locals and visitors and usually takes a prime spot in most guidebooks and promo material for the city.

Although there isn’t anything to see inside the building, there is a cute retail space at the very point of the Flatiron Building, known as the ‘Cowcatcher’. This is because the site was used as farmland long before New York’s skyscrapers arrived. Grab a postcard or enjoy the art installations that often pop up in this space.

Madison Square Park

Our second park of several along 5th Avenue is Madison Square Park. Although less famous than its counterpart further South (and nothing to do with Madison Square Garden), this urban oasis is still popular thanks to the excellent views of the Flatiron Building and, maybe just as importantly if it’s lunchtime, the world’s first Shake Shack.

The now worldwide burger brand began life as a hot dog cart in the park in 2001, before a kiosk was opened in 2004. You can still grab a top-notch hamburger and of course a cold milkshake to keep energy levels up as you head further along 5th Avenue.

Empire State Building

A view of the Empire State Building from ground level

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A short walk from MSP you’ll encounter an essential New York attraction. Yes, the National Museum of Mathematics is situated right on 5th Avenue, a great little stop before you arrive at possibly the most famous skyscraper on earth.

King Kong’s climbing frame will enjoy its 100th birthday in 2030 but she’s barely aged a day. The sleek Art Deco lines and utterly gorgeous lobby can all be visited with a relatively inexpensive ticket to the topmost viewing gallery. Hop in the lift that lifts you effortlessly 380 feet or so in the air to the 102nd floor, but you can also enjoy a bird’s eye perspective of Manhattan and beyond from 80th and 86th floors too.

The full experience includes exhibitions and even a motion simulator ride, so leave at least an hour or two of your 5th Avenue stroll to get the full Empire State Building experience. Oh, and don’t firget to book your entry tickets well in advance to save queuing on the day.

New York Public Library’s Stephen A. Schwarzman Building

A stone lion outside the New York Public Library

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You’ll probably recognise New York’s main library branch from the first Ghostbusters movie, where the huge sculpted lions (‘Patience’ and ‘Fortitude’) out front featured in several close ups. But what the film doesn’t quite get is the scale and grandeur of New York’s main public library facility both inside and out.

Pop in to take a look at the epic Map Divison, a gigantic collection of maps and globes both old and new from all corners of the world. If that’s not impressive enough, then head to the first floor DeWitt Wallace Periodical Room, home to the Declaration of Independence and the Gutenburg Bible. You can see all of this, plus a few hidden extras, on a superb free guided tour of the building departing from Astor Hall several times a day. Check the official library website for details.

Rockefeller Center

The statue of Atlas below the Rockefeller Center, New York

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The heart of broadcasting in New York City is also a prime example of epic Art Deco highrise architecture and a must-see on any NYC trip. In winter, Rockefeller Center is famous for its skating rink and gigantic tree (you’ll recognise it from Home Alone 2).

But the real reason to visit is of course the Top of the Rock, an observation deck experience which offers hands-down the best views of Manhattan at any time of day. This is where you’ll grab those amazing photos of the Empire State Building and downtown, or Central Park and Billionaire’s Row if you face North.

The Top of the Rock is always jam-packed with visitors to buy your tickets well in advance to avoid disappointment.

Saks Fifth Avenue

The exterior of Saks 5th Avenue

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5th Avenue is world famous for its shopping, and if you only visit one store on your walk, make sure it’s Saks.

Stocking fashion, accessories and other trinkets for the elite, Saks has built a reputation as the place for the super-rich and ultra-famous to be seen shopping. Even if you don’t have the budget to blow on a $500 pair of shoes, the interiors alone are good enough reason to browse and mingle with the hoity toity of New York.



St Patrick’s Cathedral

The gothic frontage of St Patrick's Cathedral New York

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Looking slightly out of place alongside the modern glass and concrete skyscrapers that surround it, this sprawling gothic cathedral dates back to 1879. Inside, you can marvel at the intricate stonework and vaulted roof, as well as the marvellous stained glass windows that bathe the cathedral in colourful light. Entry is free and you can even join a guided tour to hear the cathedral’s full story.

The Plaza Hotel and Apple Store

Manhattan's Apple Store at night with Plaza Hotel in background

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Continuing our walk northward, you’ll pass even more high-end shopping, but there’s one store that’ll catch your attention right on the corner of Central Park. Although its just your typical Apple goods store, the glass structure and underground layout make New York’s main Apple outlet a truly unique exercise in architecture that makes it stand out from the crowd.

On the other side of the road you’ll spot another famous Big Apple building – the five-star Plaza Hotel that is a key location in Home Alone 2: Lost in New York. Pop into the lobby for a spot of nostalgia, or go one step further an book the hotel’s famous afternoon tea. If you’ve gone that far, then booking a stay for the night is another option, but the waiting list for the best rooms can get quite long!

Central Park Zoo

A sea lion sits on a rock in Central Park Zoo

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This cute inner city zoo has been home to exotic species for the best part of 160 years, but after being featured in the Madagascar movie series, it has become an extremely popular tourist attraction on the edge of Central Park.

Home to snow leopards, lemurs, sea lions and of course the penguins that offer comic relief in the movies, it’s a great stop-off for kids big and small. Your Central Park Zoo ticket also includes entry in the Tisch Children’s Zoo, with petting and feeding opportunities for little ones.

The Metropolitan Museum of Art

Ancient sculptures in New York's Met

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Spanning 5,000 years of human history, New York’s Metropolitan Museum of Art covers every type of art imaginable. From ancient textiles to renaissance paintings to suits of armour to entire temples, the collection isn’t just focused on art, but equally the crafts and techniques from every corner of the planet.

If you’re a New York resident, or a student in New York, New Jersey or Connecticut, you can pay what you want to enter – and that can be $0. But if you’re visiting from elsewhere, you’ll need to buy a $30 ticket, which is a bargain in our opinion when you consider the sheer amount of incredible exhibits on offer.

Leave several hours to make the most of your ticket, or call this point the end of your walk along 5th Avenue, as there’s so much to see.

Solom R. Guggenheim Museum

New York's Guggenheim with a clear blue sky

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Known as Museum Mile, the next stretch of 5th Avenue is home to dozens of galleries, institutions and permanent and temporary exhibits. If you’re going to take time to see one, it has to be the orginal Guggenheim Museum, an extensive art gallery housed in one of New York’s, and the world’s, most unique buildings.

More spaceship than building, the Solomon R. Guggenheim Museum is a work of art in itself. Designed by legendary architect Frank Lloyd Wright, the museum took 15 years to design and build, blending elements of Art Deco and modernist architecture to create a truly unique space to showcase artworks. You’re welcome to enter and explore, but it’s just as worthwhile grabbing a spot on the sidewalk across the street and admiring the curves from afar.

Conservatory Garden

A fountain in a green park

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Although you could lose weeks of your life to every corner of Central Park, the carefully kept Conservatory Garden just up the avenue from the Guggenheim is a worthy stop off on your 5th Avenue walk. Open from 8am, there are three distinct spaces to enjoy, with fountains, flower beds and curving paths providing plenty to explore – and a handy place to catch your breath.

Marcus Garvey Park

A curved staircase in a park

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The end point of our walk along 5th Avenue is the marvellous Marcus Garvey Park at the foot of the Bronx. Although not as sculptured or expansive as other parks along the route, MGP is famous for its outdoor swimming pool which is packed out in the summer months. You can also catch performances ranging from jazz bands to Shakespeare in the park’s auditorium, so it’s a great spot to end your day after a long yet rewarding walk along 5th.

If you don’t fancy walking back to Mid or Downtown, then the Harlem-125th Street Subway Station is a short walk from Marcus Garvey Park. Or grab a cab…


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Phil Brown

Phil is the founder and lead editor at Wander Insights. A seasoned traveller, Phil has visited over 40 countries and countless incredible destinations. Favourite places include Hong Kong, Gdansk and Ko Samui.

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