In 1905, the novelist Edgar Saltus made his way to the roof of the new, twenty-one-story Flatiron Building, in Manhattan. Stunned by the strangeness of the experience—in an era before commercial aviation made it commonplace to see the world from the air—he wrote:

In the mounting wonders of the city to be, humanity will mount also. It will deny its false gods, reverse their altars, and, on the pile it has made, reconstruct Olympus. From the toppest floors you get a vision of that in the significant sunsets and prophetic dawns. You see strange things from the Flatiron.

Flatiron Building · 175 Fifth Avenue · Left: From the Metropolitan Life tower (1909), viewed here from the twenty-one-story Flatiron Building (1902), visitors could see one-sixteenth of the U.S. population. Right: One of New York’s newest skyscrapers can also be viewed through the Flatiron’s rooftop balustrade: the hundred-and-four-story 1 World Trade Center (2014).

Photograph by Pari Dukovic for The New Yorker

The rooftop observation deck is one of the city’s most distinctive architectural traditions. New York not only raised the world’s first modern skyline but pioneered a new way to see it: from a series of perches atop its highest peaks. Made possible by a revolutionary type of building invented in New York and Chicago near the end of the nineteenth century—the steel-framed, elevator-enabled skyscraper—observation decks quickly captured the city’s imagination and have been part of its history and myth ever since.

The link between deck and city became clear when, in lower Manhattan in the early twentieth century, office towers began rising higher than any buildings in history, and owners started allowing the public to visit their upper reaches—for nothing, at first, and then for a quarter. In succeeding decades, as the buildings rose higher, so, too, did the observation decks: to thirty stories, then fifty, then seventy, and, finally, a hundred stories and more. With each step upward came a more expansive view, mirroring the expansion of the urban area below—almost as if the city, as it projected outward, called for ever-higher vantage points from which its growing scale and ambition could be comprehended.

Chrysler Building · 405 Lexington Avenue · An eagle gargoyle peers out below the seventy-first-floor observatory, which opened in 1930 and closed in 1945.

Photograph by Pari Dukovic for The New Yorker

The compressed, chaotic landscape of early-twentieth-century lower Manhattan could be seen in its entirety only from the decks of early skyscrapers, like the forty-seven-story Singer Building, on lower Broadway, completed in 1908. By 1931, when the observatories of the Empire State Building opened, on the eighty-sixth and hundred-and-second floors, offering views for seventy miles, the city had grown, too, into a five-borough metropolis. F. Scott Fitzgerald visited the observation deck that year and was surprised to discover that New York “was not the endless succession of canyons that he had supposed but that it had limits.” The awful realization that it “was a city after all and not a universe,” he felt, revealed New York’s “crowning error.” By the nineteen-seventies, when the World Trade Center opened, the vista from the South Tower’s roof revealed how the city’s prewar landscape—vast but still essentially dense—had been transformed into a sprawling, largely suburbanized “region.”

As the observation decks rose higher and became larger, reflecting the bigger footprints of the office towers below, they evolved in style. The earliest ones were narrow, precipitous, almost improvised spaces, tucked into the classical campaniles and Gothic belfries that topped those pioneering buildings; the decks were reached through tiny penthouse elevators and steep staircases, in a staged ascent not unlike mountaineering. By the nineteen-thirties, there were Art Deco towers crowned with dreamy cloud rooms, half a dozen in all, floating above the city, sleek, glamorous realms of the sort associated with Fred Astaire and Ginger Rogers.

City Bank–Farmers Trust Company Building · 20 Exchange Place · Though open to the public for only a few years after its opening, in 1931, the deck and arcade atop the City Bank–Farmers Trust Company Building offered a series of exquisitely framed rooftop scenes, ranging from thrilling closeup views of the new towers of lower Manhattan to serene distant vistas of New York Harbor.

Photograph by Pari Dukovic for The New Yorker

The views available through the wedge-like windows of the spire of the Chrysler Building (1930) were limited, but the interior observation room, on the seventy-first floor, offered high, crazily angled walls, painted stars, and hanging Saturn lamps suggesting a celestial platform linking Earth to the heavens. The architects of the observation gallery in the nine-hundred-and-fifty-two-foot-tall Cities Service Building (1932), at 70 Pine Street, created a luminous, airy space whose skylighted roof and perimeter of glazed French doors allowed visitors to feel as if they had left the city entirely. (Even the elevator disappeared discreetly into the floor.) The terraces of 30 Rockefeller Plaza (then called the RCA Building), finished in 1933, and stretching half a block east and west, were compared to the promenade deck of a transatlantic ocean liner, and provided rows of Adirondack chairs for sunbathers and umbrella-shaded café tables for brown-bagging workers. The eighty-sixth floor of the Empire State Building had an Art Moderne observation lounge containing a panelled “writing room,” for addressing postcards, a tearoom, and a “sunset lounge,” whose Belgian-marble bar served five kinds of champagne, along with a house cocktail, the Empire State, made with Amstel bitters, orange bitters, French vermouth, Scotch, and dry gin.

Thanks to its unrivalled height, and to “King Kong” (1933), the building became an instant worldwide icon, extending its fame with a parade of celebrity visitors (Albert Einstein, George Bernard Shaw, Queen Elizabeth II) and publicity stunts. The tiny balcony on the Singer Tower had accommodated forty people; the Empire State, which turned its entire quarter-acre roof over to the public, hosted nearly a million people in its first year. Once the province of local visitors, the New York observation deck had become a mass tourist attraction. In 1975, when the enclosed portion of the Top of the World observatory opened, on the hundred-and-seventh floor of the World Trade Center’s South Tower, its rubber-mat floors and steel-mesh benches evoked a high-school gym more than the Queen Mary. This was a facility shaped to the demands of processing eight thousand tourists a day rather than offering respite to sun-seeking office workers.

Cities Service Building · 70 Pine Street · The observation deck (1932) featured open railings intended to let in the breezes of the Upper Bay.

Photograph by Pari Dukovic for The New Yorker

Not even the awful images associated with September 11, 2001, dampened the public’s appetite for standing atop a skyscraper. By 2012, the Empire State Building’s newly remodelled observation deck was hosting eleven thousand visitors a day, bringing in more annual revenue than all the building’s floors of rented office space combined. The Rockefeller Plaza deck reopened in 2005, refurbished as Top of the Rock. Last year, the One World Observatory, a huge, enclosed operation, was unveiled at 1 World Trade Center—the first new observation deck to be built in the city in forty years. The observation deck planned for 30 Hudson Yards, now under construction, includes a prowlike open-air platform cantilevered over the side of the tower, a kind of reinterpretation of the vertiginous spirit of Manhattan’s earliest observation decks. Downtown, the intricate complex of rooftop galleries and terraces on the Cities Service Building is being renovated into a three-story lounge and restaurant.

In a world of digital simulation, what is the enduring attraction of actually standing on a high building and looking out on the city? Being on top of a skyscraper creates a sense of transcendence: the swift rise from the busy streets to an environment whose character owes less to the city below—its roar reduced to near-silence—than to the sensations of wind and air and sunlight. (It is this spirit, perhaps, that led movies from “On the Town” and “An Affair to Remember” to “Sleepless in Seattle” to co-opt these engineering marvels as magical settings for romance.) There is also a sense of power, as you comprehend, with sudden clarity, the dense and complex landscape of the modern city. “Your elevation transfigures you,” the French philosopher Michel de Certeau wrote in the late seventies, after a visit to the World Trade Center. “It transforms the bewildering world by which you were ‘possessed’ into a text that lies before your eyes. It allows you to read it, like a solar eye, looking down like a god.”

Empire State Building · 350 Fifth Avenue · The observation deck, opened in 1931, was known for its celebrity visitors, from Josephine Baker to Groucho Marx.

Photograph by Pari Dukovic for The New Yorker

This double identity—a place set halfway between the worldly city and the infinite sky—caught the imagination of Helen Keller, an early visitor to the Empire State Building. Standing on the observation deck, Keller had an experience beyond sight. “The little island of Manhattan, set like a jewel in its nest of rainbow waters, stared up into my face, and the solar system circled about my head,” she wrote afterward. “Why, I thought, the sun and the stars are suburbs of New York, and I never knew it! I had a sort of wild desire to invest in a bit of real estate on one of the planets.”