Company Logo - Home Link

Flatiron District NYC | Things to Do

Updated: October 3, 2021

This Flatiron District walking tour is a self-guided tour of one of New York City's iconic neighborhoods. The Flatiron District gets its name from it's most famous skyscraper residents, the Flatiron Building.

However, the neighborhood is home to several iconic NYC skyscrapers as well as one of the city's most visited parks, Madison Square Park, with its green spaces and public monuments and statues - not to mention the 1st ever Shake Shack.

This tour will take you approximately 90 minutes, though you might want to take a seat on one of the many park benches and take part in a New York City pastime - people watching.

Click here for a larger interactive map.


Flatiron District Tour Map


Click here to view this tour as a PDF to download to your smartphone.

Click here for hotel suggestions in the area. You might consider taking this tour along with our self-guided Gramercy Park and Union Square Tour. Be sure to check out our full list of self-guided walking tours in New York City

Where is the Flatiron District?

The Flatiron District is centrally located on the island of Manhattan on the southern border of Midtown Manhattan.  

Centered by Madison Square Park, this neighborhood stretches south-north from 20th till 26th Street and east-west from 6th Ave to Lexington Ave. 

It's easiest to reach the district by subway from the E. 23rd Street Station (N + R lines) and the 6 train on the Lexington Line.  

There are other stations within reasonable walking distances as well as bus lines.  

We recommend using this link for directions to the Flatiron District. Be sure to read our posts on navigating the New York City subway and getting help with buying a MetroCard.

TIP: If you are considering using one of the hop-on, hop-off buses to transport you around NYC, keep in mind that all 3 major operations have stops in the area. Read our post comparing the different bus tour options.


1) Flatiron Building 

Flatiron Building New York The best place to start is the unique building for which the entire area is named. This building was considered groundbreaking for its time.

Using an interior steel skeleton enabled architect Daniel Burnham to create the 21 story building that stands today.

It was one of the tallest buildings in the world when it was completed in 1902 and was one of two skyscrapers north of 14th Street at the time.  

It is also one of our 10 most famous New York skyscrapers. 

The building was originally called The Fuller Building after George S. Fuller, the inventor of modern skyscrapers and the modern contracting system for building projects.

The name of the building did not last long, though. Residents of New York thought that the building resembled a cast-iron clothes iron and the nickname “Flatiron Building” stuck. The name has been officially changed.

Some Other Facts About The Flatiron Building

  • The building is 285 feet tall
  • The vertex of the building is only 6.5 feet wide (about a 25 degree angle)
  • The steel for the structure had been pre-cut very precisely. This enabled the workers to build an average of one floor per week.
  • Because of the unique shape of the building, the wind sweeps around the sides and creates powerful gusts.
  • It is said that the origins of the phrase “23 skidoo” came from this building. Police officers would yell this at men hanging around the building hoping to see the wind blow ladies skirts up.
  • The Flatiron Building is shown to be the headquarters of The Daily Bugle, the fictional newspaper that Peter Parker works for in the Spider-Man movies.

Both Gray Line and Big Bus hop-on, hop-off companies have stops here.  Read our post comparing the different bus tour options.

2) Madison Square Park

Directly across the street from The Flatiron Building is Madison Square Park. This area has gone through many Madison Square Park New York Flatiron District Tour different incarnations throughout the city’s history.

It was a hunting ground in the early days of New York and became a potter’s field in the 1700’s (a common grave for the poor.)

An arsenal was later built there, followed by a Juvenile detention center and, finally, in 1839, a roadhouse named Madison Cottage.

This was the extreme northern end of the city at this time, so the roadhouse was the last stop for those headed out of the city and the first stop for those headed in.

Madison Cottage was named for the fourth president of the United States, James Madison.

The cottage gave its name to Madison Avenue and Madison Square Park, which was later built on the site.

Other Madison Square Park Facts

  • To generate interest in The Statue of Liberty, the arm and torch of the statue were assembled and kept in Madison Square Park between 1876 and 1882.
  • One of the first professional baseball teams, The New York Knickerbocker Base Ball Club, has its roots in the park. They played in a vacant sandlot at 27th and Madison starting in 1842.
  • In the middle of the eastern edge of the park is an oak tree. In 1936, for the centennial anniversary of Madison Avenue, the tree was donated from Montpelier, the Virginia estate of James Madison.

3) Eately

If you are an Italian food lover, this is not to be missed! This 50,000 square foot (5,00 sq m) space combines an Italian specialty grocery store with tasting rooms.

The original Eataly was opened in Turin, Italy in a converted vermouth factory. Businessman Oscar Farinetti opened the New York location with a team of partners, including Mario Batali.

Eatlay opened in 2010 and has been bustling ever since! Options for tasting rooms include a wine bar, pasta restaurant, pizzeria, a seafood restaurant, gelato and more!

For the true gourmet, there are classes and events held in the store.

4) William Seward Statue

This statue is of former Governor of New York, United States Senator and Secretary of State William H. Seward.

William Sewerd Statue Madison Square Park

Seward was an outspoken abolitionist and was actually considered the leading candidate for the Republican Party for the presidential nomination for the Election of 1860.

Abraham Lincoln was the nominee instead. Though this was a blow to S

eward, he campaigned heavily for Lincoln throughout his campaign.

When Lincoln was elected, Seward was named Secretary of State. He served throughout Lincoln’s presidency and then under Andrew Johnson after Lincoln’s death.

The statue was placed in Madison Square Park in 1876, and it is said to be the first monument to a native-born New Yorker in the city.

5) Shake Shack

At the Southeast corner of the park is the original Shake Shack. Shake Shack today has 63 locations worldwide, but it all started as a seasonal food stand in this park in 2000.

It was a part of the Madison Square Park Conservancy project, designed to help boost the first art installation sponsored by the organization.

It was a huge success, so they brought the stand back for the next few summers.

This eventually turned into the permanent structure in this park and an entire restaurant chain.

6) One Madison Park

One Madison Park New York City The sleek, modern-looking tower on the southwest corner of the park is One Madison Park. Originally intended to be 47 stories, the completed tower has 60 stories.

There are 53 units with beautiful, 360 degree city views.

The 6,850 square foot penthouse apartment was originally listed for $45 million dollars and was advertised as including a butler (who would live-in in another apartment in the building.)

The building had some financial problems at first, but was widely praised for the architecture.

Notable residents include Patriots quarterback Tom Brady and supermodel Gisele Bundchen, Rupert Murdoch and Peter Buffett (son of billionaire Warren Buffett.)

7) MetLife Tower and MetLife North Building/Credit Suisse

Metlife Building Madison Square Park The beautiful, Italian Renaissance-style clock tower was the tallest structure in the world when it was built in 1909.

It is also one of our 10 most famous New York skyscrapers. It was an addition to the smaller, 11-story building that once stood alone on the site as the Metropolitan Life Home Office. (The original building was completed in 1893).

The tower is 50 stories and the four faces of the clock are each 8 meters in diameter (26.5 feet).

The gilded cupola at the very top is always illuminated, even after the other building lights are turned off.

The tower today is being converted into a hotel.The building directly north, at 11 Madison Avenue, is called the MetLife North Building or 11 Madison.

The 30-story art-deco skyscraper began construction in the 1920’s. The original design was for a 100 story building that would have been the tallest in the world.

When the stock market crashed and the Great Depression began, construction was halted at only 29 floors in 1933.

The building wasn’t “completed” until 1950, and there are no known plans to ever add the 70 other planned floors (though the current building would be strong enough to support them.)

The original plans also called for a subway station under the building, but it ended up one block south.

The grand lobby features beautiful limestone and marble and has 30 elevators- enough to accommodate the planned 100 floors. The building was the MetLife records department for many years, and today is primarily occupied by Credit Suisse.

8) New York Life Insurance Company

New York Life Insurance Building Flatiron District Madison Square Park The building to the north of the park with the gold, pyramid-shaped roof was built as the headquarters of the New York Life Insurance Company.

The building was designed by Cass Gilbert, who also designed the Custom House and the famous Woolworth Tower as well as the United States Supreme Court Building in Washington, DC.

This 40-story building occupies an entire city block and was the last significant Cass Gilbert skyscraper in New York, completed in 1928.  

Before this building was here, this was the site of the passenger depot for the New York Harlem and New York New Haven Railroads.

Later it became the site of the first two Madison Square Garden arenas. The second Madison Square Garden was designed by Stanford White, who kept an apartment in the building.

He was shot in the rooftop restaurant of the building by Harry K. Thaw over an affair with Thaw’s wife. The ensuing trial and media frenzy surrounding it was called “The Trial of the Century.”

The current Madison Square Garden arena is the fourth (the third was at 8th Avenue and 50th Street) and has kept the iconic name even though it is not located at Madison Square Park.

9) Eternal Light Flagstaff

General Worth Monument Madison Square Park Flatiron District New York City

This pink granite flagstaff was commissioned by department store magnate Rodman Wanamaker for $25,000.

It was dedicated on November 23rd (Armistice Day) in 1923 and was in honor of members of the United States Army and Navy who were received at that site at the conclusion of World War I.

Open Loop, a hop-on, hop-off bus company has a stop here.

Read our post comparing the different bus tour options.

10) General Worth Square

At the northern end of this park is an area called General Worth Square. Head up there to see the obelisk that was built in 1857 in honor of General William Jenkins Worth, who served in the Seminole Wars and the Mexican War.

The city of Fort Worth, TX is named after General Worth. This was one the first monuments in a city park since the statue of King George III had been removed from Bowling Green in 1776.

It is the only monument in New York besides Grant’s Tomb that doubles as a mausoleum.

11) National Museum of Mathematics

Change the way you (or your children) look at math!! This museum, which was established in 2009, strives to educate the public about the patterns and mathematics in the world around us.

The current museum began after a smaller math museum was closed on Long Island. It was realized that there were then no mathematics-based museums in the United States.

The current space has 19,000 square feet of exhibits, including many that are hands-on.

It is open seven days a week, from 10am to 5pm. Prices are:Adults: $15.00, Children, Students and Seniors: $9.00.

12) Farragut Statue

Though you may not have heard of this man, you have probably heard a phrase he is famous for. Admiral David Glasgow Farragut began his military career at the age of 9.

Farragut Statue Madison Square Park

He was a midshipman during the War of 1812, fought Caribbean pirates in the 1820’s and later fought in the Mexican War.

At the onset of the Civil War, his Union allegiances caused him to move from Virginia to New York State. He fought for the Union and helped take control of New Orleans.

He and his troops accomplished a seemingly impossible feat when they won the Battle of Mobile Bay. It was there that he was said to have shouted, “Damn the torpedoes!

Full speed ahead!” His statue was sculpted by Augustus Saint-Gaudens and was dedicated in 1881.

13) Chester A Arthur Monument

Chester A Arthur Statue Madison Square Park This statue is of Chester A. Arthur, 21st President of the United States. Arthur moved to New York City as an adult to practice law.  

HE was a staunch abolitionist and was known for taking on civil rights-related cases. he was involved in one particular case that ended up paving the way for the integration of passenger trains in the city.  

He served the Union during the Civil War and was in charge of providing equipment, clothing and supplies to New York State's troops.  

Having been active in the Republican party for many years, Arthur was added as the Vice-Presidential nominee alongside James Garfield in 1880.  

When Garfield was assassinated in 1881, Arthur assumed office. He was in New York at the time, making him the first President since George Washington to be sworn in in NYC.

During his presidency, he successfully supported the Civil Service Reform Act of 1883 and vetoed legislation that would limit Chinese laborers immigrating to the United States.  

He was not nominated for re-election, so he returned to New York City, where he died in 1886. The monument was commissioned by his friends and cost $25,000.

It was dedicated June 13, 1899.

14) Museum of Sex

This museum opened October 2, 2002. Since then, they have been shaking up people's perceptions of what a museum is. The museum is designed to highlight the cultural significance and the history of human sexuality.  

They have a large collection of artifacts, ranging from photographs and art to clothing and costumes.  

They are also committed to preserving pieces that may have otherwise been discarded due to their sexual content.  

The museum is open Sunday-Thursday from 10am to 8pm and Friday Saturday from 10am to 9pm.  

Tickets are $17.50 for adults and $15.25 for Students and Seniors with ID. People under 18 years of age are not permitted.

Open Loop, a hop-on, hop-off bus company has a stop here. Read our post comparing the different bus tour options.

15) Herman Melville House

104 E 26th St- Though this is an office building today, there was once a single-family brick house on this site. It was the hoem of American novelist Herman Melville and his family for the last 28 years of his life.

Melville was born in Lower Manhattan, on Pearl Street. He spent some time in New England, which is where he wrote his classic Moby Dick, but he made his way back home to New York and lived on E. 26th Street.

In his house here he wrote his second best-known work, Billy Budd, as well as many works of poetry.

Hotels and Accommodations in the Flatiron District

You might start your hotel research by checking out the 30 Flatiron District hotels as filtered by TripAdvisor. Another way is to check our filtered list for the Flatiron District.  

You could read the reviews before you book. We also have put together a section on our budget guide to help visitors to New York find affordable accommodations.  

Below are some of our suggestions for accommodations in or around the Flatiron District.

Our picks:


Back To Top


About The Author

Stephen Pickhardt

Stephen is the CEO of Free Tours by Foot and has overseen the transformation of a local walking tour company into a global tour community and traveler’s advice platform. He has personally led thousands of group tours in the US and Europe, and is an expert in trip planning and sightseeing, with a focus on budget travelers. Stephen has been published and featured in dozens of publications including The Wall Street Journal, BBC, Yahoo,, and more.
Updated: October 3rd, 2021
Back to Top