Flatiron Building, New York City: Things to see and do in the Flatiron District

There are much more imposing structures in New York City than the 22-storey Flatiron Building. The Chrysler building is arguably the most beautiful. The Empire State Building remains the most famous. And the Twin Towers, like Pearl Harbour before it, are remembered, for a similarly horrific and surprise attack on September 11, 2001. And now the One World Observatory's 100-storey viewing deck offers a 360 degree vista of all five New York City boroughs, plus much of New Jersey.

"But only one building in New York has an entire district named after it," says Rory Lipede, our charismatic guide. "And that's the Flatiron."

Contrary to popular belief, New York wasn't the first city to have skyscrapers, Lipede explains. "That was Chicago. The Flatiron, completed in 1902, wasn't even the first skyscraper in New York but it was easily the most distinctive." Built on a triangular plot of land, where the rigidly straight Fifth Avenue collides with the meandering Broadway, its shape is reminiscent of an old-fashioned steaming iron.

Usually Lipede's three-hour walk-and-taste tour begins outside the Flatiron but this morning there's a problem on the subway, so she meets our group at nearby Union Square, which makes more historical sense since it marks the outer southern edge of what's known as the Flatiron District and allows our stroll to follow architectural chronology.

With its statue of Abraham Lincoln and its history as the starting point for New York protest marches, Union Square is also the site of a year-round Greenmarket, dating back to 1976. On this autumn day, it's full of stalls selling fruits, vegetables and artisan foods from farms and niche producers in the surrounding areas,most notably, giant Halloween pumpkins.

One seafood stall sells blowfish, which I thought were either poisonous or protected. "They're called chicken of the sea," the grandmotherly stallholder says. "I dust them in flour, then pan fry them. They have a central bone so you eat them like a chicken wing."

At the point where Broadway crosses East 17th Street, Lipede stops our group. "This was known as the Ladies' Mile," she says. "It was the birthplace of the first department stores in the world."

Thanks to cast iron construction, towering buildings (some up to six floors high!) could house everything an affluent 19th-century woman could possibly want to buy under one roof. The building's cast iron corsets were hidden under frilly facades. Lipede points out three types of architecture the district is known for: German Gothic, Italianate Beaux-Arts and chateaux Parisienne.

"Is it too early for a cheese tasting?" she asks, beckoning the group inside Beecher's Handmade Cheese factory. "We usually do this as our last stop."

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It's hard to imagine there's actually a boutique cheese factory, restaurant and bar (with "ageing room" and regular wine and cheese tasting sessions) in Manhattan. And for that, Lipede insists, we should thank Beauty and the Beast. Disney's 1991 movie was the first cartoon musical to become a Broadway hit, but only because Disney insisted the rundown Times Square theatrical district, then known for its sleaze, be cleaned up first.

Emboldened by the clean-up of Times Square, the New York City Landmarks Preservation Commission – established in 1965 by Mayor Robert Wagner following the catastrophic decision to demolish Pennsylvania Station – was suddenly able to expand its brief to protect architectural and culturally significant buildings in other parts of the city.  . Hence this cheese factory. I recommend the Flagship hard cheese while watching future batches being made below.

Once outside, it's a five-minute stroll to the actual Flatiron Building, but Lipede stretches it into an entertaining half hour.

"This was a race to the sky," she explains as we pause for the first time in front of the Flatiron. Its official title was the Fuller Building, named after its original tenants, but locals never called it that. They knew it as "the stupid flat iron block" long before building even began, Lipede explains. No one thought a profit could be made from such an awkward plot except for Chicago architect Daniel Burnham. Burnham, who was among the first to build America's skyscrapers, saw an opportunity to create a structure where none had been thought possible.

Lipede herds us across 23rd Street into the confines of Madison Square Park to get a classic view of the Flatiron, and points out Burnham's architectural signature. Unlike most skyscrapers of the era, the Flatiron was not grounded with a monumental base, but seemed to soar out of the landscape. There's the three-storey base, then the elegant shaft of the building with its repetitive fenestration and decorative patterns. And finally, the four-storey capital. A two-storey condo – which last sold in 1999 for $US23 million and has its own lift – sits at the top.

One of the drawbacks of such a tall triangular building being built at this intersection was the creation of a strong wind that whipped around its corner raising women's skirts and exposing (shock, horror!) their ankles and calves. Lipede suggests this may have been the origins of the phrase "23 skidoo", American slang for men being forced to leave the scene of a real or potential crime before they were arrested.

The cost of living in the Flatiron is not as high as you might imagine. During the Great Depression, rents were set for "single room occupancy" (SROs) and in the case of the Flatiron, that meant a single room with sink plus one bathroom a floor (male and female on alternate levels). Occupancy could only be handed down through family ties and no renovations were allowed. Today's rent in a Flatiron SRO sits at $US125 a week.

Lipede's tour could continue for hours, but we're in a New York rush so we wind up at Eisenberg's Sandwich Shop, whose motto is "Raising New York's cholesterol since 1929", and whose menu reads like a Billy Crystal monologue.

According to Lipede, Eisenberg's is one of the oldest classic Jewish-German diners left in Manhattan. I order its reuben sandwich: pastrami with Swiss cheese, sauerkraut, Russian dressing and pickles, "grilled on rye". Plus an Arnold Palmer (half iced tea, half lemonade).

Pinch me. Am I really in Manhattan, or just dreaming?

TRIP NOTES

Steve Meacham was a guest of Singapore Airline and Like A Local Tours.

MORE

See traveller.com.au/USA

TOUR

Like A Local Tours. See likealocaltours.com

FLY

Singapore Airlines flies from Singapore to Newark Liberty International  three times weekly. See Singaporeair.com

STAY

Millennium Broadway See: millenniumhotels.com

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