New York City Audio Tour: Midtown East Gems

Look to your right at this towering eighteen-story limestone building, easily spotted by its elegantly curved corner, deep horizontal grooves across its lower base, and the ornate carved stone garlands draping down its sides. This is the St. Regis New York, an absolute masterpiece of the Beaux-Arts style, which is a grand, heavily ornamented French architectural tradition. Over a century separates the views of this enduring elegance standing tall as the surrounding cityscape transformed from horse-drawn carriages to modern traffic, so tap the before and after image in your app to take a look. John Jacob Astor the Fourth opened this place in nineteen oh four. Now, Astor had two huge motivations here. First, he desperately wanted to outshine his cousin, who had just built the rival Waldorf-Astoria. Second, Astor needed a sanctuary. He had just outraged New York high society by divorcing his first wife and marrying a nineteen-year-old, so he figured he would just build his own private clubhouse to escape the glaring eyes of the elite.

His wealthy neighbors were absolutely furious. Oil tycoon William Rockefeller led the charge, branding the towering hotel a social crime that would bring unpredictable strangers into their exclusive enclave. Rockefeller and his millionaire buddies even planted bizarre rumors in the newspapers to scare away potential guests. They claimed the hotel charged visitors by the foot for filtered air, and that a simple chocolate eclair would cost five hundred dollars, which is about seventeen thousand dollars today. The smear campaign got so bad that the hotel manager had to issue public denials.

But Astor had the last laugh, filling the hotel with mind-blowing technology for the era. He installed an incredible central vacuum system where maids simply plugged flexible hoses into wall sockets that whisked dust directly down to the basement.

He also commissioned artist Maxfield Parrish to paint the famous Old King Cole mural for the bar, paying him five thousand dollars, roughly one hundred and seventy thousand dollars today. Parrish actually hated Astor's demanding attitude, so he took a subtle, hilarious revenge. If you ask the bartenders today, they will tell you that the smirking courtiers in the painting are reacting because Parrish secretly painted the King in a state of flatulence.

Tragically, Astor died on the Titanic in nineteen twelve, though survivors remembered him calmly smoking a cigar and heading down to free his dog, Kitty, before the ship sank.

His beloved hotel lived on to host a wildly colorful cast of characters. In the nineteen sixties and seventies, the surrealist painter Salvador Dalí lived here every winter. Dalí would casually walk his pet ocelot down the marble corridors on a leash. He even found a genius way to avoid paying his massive room service tabs. He would pay with personal checks that he had embellished with original sketches, knowing full well the management would rather frame his artwork than cash the checks.

Meanwhile, director Alfred Hitchcock maintained a favorite suite where he once devoured three full steaks and three portions of ice cream in a single sitting. And in nineteen seventy-one, John Lennon hunkered down on the seventeenth floor, happily sitting on the carpet to sort a massive delivery of Elvis Presley records, and practicing on a typewriter by repeatedly typing the phrase, I am a pimp.

From feuding millionaires to surrealists with wild cats, the walls of the St. Regis hold some of the best gossip in the city. Enjoy the lavish details of the facade before we move on to our next destination.

Look to your left to spot the striking New Jersey red sandstone facade of the Fifth Avenue Presbyterian Church, easily recognizable by its pointed Gothic arches and a towering spire featuring a prominent clock face. Take a glance at your screen to see a great wide shot of this magnificent exterior.

Back in eighteen seventy-three, the congregation bought this undeveloped plot and dropped a cool one million dollars on construction-about twenty-eight million dollars today-aiming to build a cathedral in what was then a quiet, wealthy residential area called Millionaires Row. They spent so much because they genuinely believed the newly built Central Park would act as a permanent fortress, blocking the loud, industrial chaos of lower Manhattan from ever reaching their doorstep.

They hired a relatively unknown thirty-seven-year-old German architect named Carl Pfeiffer. Pfeiffer pulled off an incredible architectural magic trick by designing a building within a building. The walls of the sanctuary inside actually do not touch the exterior stone walls you see from the street. A layer of air separates them, acting as a thermal and acoustic shield against the city noise. If you pull up the second photo on your app, you can see the gorgeous interior with its sloping floor and curved pews, designed so that a whisper from the pulpit reaches the very back row.

That soaring clock tower holds a mechanical rarity. It is one of only two manually wound tower clocks left in New York City, meaning every single week, a staff member hikes up there to wind the heavy weights by hand. Talk about getting your steps in. Noticeably absent from that tower are bells. When the church opened in eighteen seventy-five, Saint Luke's Hospital sat directly across the street, and church leaders deliberately left out the chimes so they would not disturb the resting patients.

This congregation has never shied away from shaking things up, though. In nineteen fifty-six, Pastor John Bonnell noticed how isolated city dwellers felt and launched Dial-a-Prayer, a dedicated phone line playing a recorded prayer. It became an overnight sensation, requiring a whole bank of phone lines just to handle the traffic.

Decades later, in two thousand and one, the church made headlines by suing the City of New York. The police had started forcibly removing homeless individuals who slept on the church steps. The church argued that sheltering the vulnerable was a core religious practice protected by the First Amendment, the part of the United States Constitution guaranteeing the free exercise of religion. A federal judge agreed, ruling that the elevated steps were a private religious space, allowing the church to continue its physical sanctuary while the city kept the public sidewalks clear.

This grand house of worship welcomes visitors most days from nine A-M to six P-M, with shortened hours on weekends. Take a moment to admire the stonework before we move along. Whenever you are ready, we will head toward our next stop.

Look for the narrow limestone building featuring a striking, arched window separated by columns on the second level and decorative carved ledges stretching across the upper floors.

This is number ten West Fifty-Sixth Street. Back in eighteen ninety-nine, a stockbroker named Frederick Edey and his socialite wife, Birdsall, bought this lot. Frederick and his business partner, H-B Hollins, bought adjacent lots, planning to build twin mansions side by side.

Hollins started building immediately next door at number twelve. But Frederick hit a snag. An old property covenant, a legal restriction tied to the deed, prevented him from building all the way to the sidewalk for two whole years. Hollins just kept building, leaving Frederick staring at an empty dirt patch.

By the time the Edeys could finally build in nineteen zero one, they ditched Hollins's architect and hired the firm Warren and Wetmore instead. The original construction cost was fifty thousand dollars, which is roughly one million eight hundred thousand dollars in today's money. They built this six-story French Renaissance Revival townhouse, a style inspired by grand European chateaus, giving it a much more rigid, formal look than the neighbor's house. You can check your screen to see a photo of these two completely mismatched buildings side by side. An architecture critic once described their contrasting styles as an uneasy dance, with one house doing the lively cancan and this one doing a stiff minuet.

The Edeys finally moved into their grand home in nineteen zero three, complete with an elevator and ten servants. If you pull up the before and after pictures in the app, you can see how this pristine facade looked back then compared to the modern towers surrounding it today. The Edeys threw grand parties here, but the house is also famous for a truly bizarre burglary in nineteen twelve. A thief broke in, locked a servant in a closet, and then fled the scene stealing absolutely nothing except the key to that very closet door. I guess he just really hated open doors.

By nineteen nineteen, Midtown was becoming a busy commercial zone, and the Edeys sold the house. Over the next century, it transformed into a high-end dressmaker shop, a cosmetics headquarters, and eventually a retail space arranged entirely by feng shui principles, the ancient Chinese practice of harmonizing individuals with their surrounding environment. It even hosted Hollywood royalty, as the actress Elizabeth Taylor lived right here for a few years in the mid-nineteen fifties.

More recently, in twenty eleven, Mexican billionaire Carlos Slim bought the townhouse for fifteen million five hundred thousand dollars. He leased it to a luxury hair salon for over a million dollars a year, but the salon stopped paying rent. Slim had to drag them to court twice just to get them out and recover his money.

Even billionaires have landlord troubles, but at least they own a magnificent piece of architectural history. Take your time admiring this surviving mansion, and when you feel ready, continue along the route.

Look up to your right and you will spot a soaring, ultra-thin rectangular skyscraper defined by a stark, repeating grid of square windows cut into poured white concrete. This is Four Hundred Thirty-Two Park Avenue, a defining pillar of Billionaires Row reaching an astonishing one thousand three hundred ninety-six feet into the sky. If you check your screen, you can see how this supertall marvel transformed from an exposed concrete framework surrounded by construction scaffolding into a gleaming, completed residential tower with its signature grid-like facade.

Developer Harry Macklowe and architect Rafael Viñoly designed this pinnacle of extreme wealth. Viñoly famously admitted that the rigid, regular lattice design was actually inspired by a nineteen oh five Austrian trash can. The public has been less kind, giving it nicknames like The Awful Waffle and The Middle Finger. You can pull up your app to see its stark, slender profile towering defiantly over the neighborhood, which many consider an architectural emblem of rising inequality.

When completed in two thousand fifteen, it was the tallest residential building in the world. Units sold for anywhere from ten point five million to over ninety million dollars. But living in a pencil tower comes with a unique set of terrifying perks. Its height-to-width ratio is fifteen to one, making it incredibly slender. Those empty, double-story floors you see every twelve levels are windbreaks meant to stop the building from swaying. They did not entirely work.

Residents describe the experience of living up there as downright eerie. When the wind picks up, the metal partitions inside the walls groan and vibrate so violently that water sloshes right out of the bathtubs. Elevators frequently break down during high winds. On Halloween night in twenty nineteen, the system glitched, trapping a resident inside a stalled car for an hour and twenty-five minutes. And then there is the garbage chute. Because the drop is so massive, bags of trash plummeting from the top floors sound like a bomb detonating when they finally hit the bottom. Talk about a rude awakening.

The ultra-wealthy occupants were furious. In twenty twenty-one, the condo board sued the developers, citing one thousand five hundred structural flaws. There were reports of giant cracks in the facade, some up to ten inches deep. Harry Macklowe reportedly offered a creative fix for the cracking concrete. He suggested applying a clear silicone finish, exactly like the one he used to coat his twenty-five million dollar personal sailing yacht. The board, quite sensibly, flatly rejected the idea.

While the building and its private staff operate twenty-four hours a day, the drama over this colossal luxury experiment never seems to sleep. Gaze up at this modern monolith as long as you like before we continue our walk.

Look to your right, and you will spot a towering, tiered skyscraper featuring a dark stone base framed by large geometric window grilles, rising into a striking white brick tower with stepped setbacks. Long before this Art Deco beauty stood here, this corner belonged to a formidable New York socialite named Mary Mason Jones. Her father bought this plot in eighteen twenty-five for just fifteen hundred dollars, which is roughly forty-five thousand dollars today. At the time, people thought he was crazy to buy land so far north. But Mary, who inspired the grand matriarch in Edith Wharton's classic novel The Age of Innocence, had the last laugh. She built a massive marble mansion right here and quite literally sat by her window, watching as the city's elite slowly moved uptown to be her neighbors.

Fast forward to nineteen thirty, when developer Abe Adelson and architect Ely Jacques Kahn built the four hundred thirty-five foot skyscraper you see now, originally called the Squibb Building. Adelson was a forward thinker. Pull up your screen for a second to see what I mean. This exterior view of seven forty-five Fifth Avenue highlights its iconic corner windows, a pioneering architectural choice in New York City skyscrapers intended to maximize light and provide Central Park views. Adelson even leased the lot next door just to make sure no one would ever build high enough to block his northern exposure. Talk about protecting your investment.

Kahn, the architect, loved his design so much that at a nineteen thirty-one architectural costume ball, he actually dressed up as the building. Picture this grown man in a white suit with a massive, tiered headpiece mimicking the building's top setbacks, standing next to another guy dressed as the Chrysler Building.

Over the decades, the tenant list inside these walls has been wildly entertaining. You had the famous toy store F-A-O Schwarz operating here for over fifty years. Following World War Two, the New York Yankees ran their executive business offices in the building. In nineteen forty-five, a young Yogi Berra walked into those offices while on weekend liberty from the Navy. The Yankees' president took one look at his short, stocky frame and openly lamented that he had just turned down a fifty thousand dollar offer from the rival New York Giants to take Berra off his hands. Obviously, Yogi went on to prove him very wrong.

Down on the ground floor, you also had Reuben's Restaurant, a legendary deli that moved in during nineteen thirty-five. It became a massive hub for the theater and film crowd. This was the very place where socialites and celebrities would chow down at midnight, helping to cement the fame of the classic Reuben sandwich we all know and love.

It is quite a legacy for one piece of real estate, going from Gilded Age mansions to skyscraper costumes, baseball legends, and pastrami. Take one last look at those iconic corner windows, and when you are set, let us keep moving.

Look to your right and you will spot a tiered granite fountain featuring a wide circular basin, crowned by a dark bronze statue of a woman holding a basket. This is the Pulitzer Fountain, named for the legendary newspaper publisher Joseph Pulitzer, who died in nineteen eleven and left fifty thousand dollars, which is roughly one point six million dollars today, to build it. Pulitzer specifically wanted his fountain to look like the grand ones in the Place de la Concorde in Paris, France.

The executors of his estate held a massive design competition, and architect Thomas Hastings won the job. Hastings designed the magnificent structure you see before you, but the crowning glory, the statue of Pomona, the Roman goddess of fruit and abundance, came with a bit of a tragic backstory. Sculptor Karl Bitter designed the allegorical bronze figure, which is a piece of art meant to represent a broader concept like abundance, using a woman named Doris Doscher as his model. Bitter finished the plaster cast in April nineteen fifteen, but he died unexpectedly before he could cast it in bronze. If you look at your app, you can see a historical photo of that exact unfinished plaster cast. After Bitter passed away, his widow and the architect brought in another sculptor named Isidore Konti to complete the actual bronze statue. They finally dedicated the fountain in May nineteen sixteen, and local newspapers proudly declared it was bubbling with the purest water in the city.

Over the decades, the fountain required a few expensive facelifts. The original limestone basin was swapped for Italian marble in nineteen thirty-five, and finally rebuilt in sturdy granite during a massive restoration project that wrapped up in nineteen ninety. Before that nineteen ninety overhaul, the fountain had lost its magic and merely dripped and dribbled a sad stream of water. The restoration completely updated the mechanical systems, allowing the water to cascade exactly as intended, giving the plaza a brilliant rushing sound. Take a peek at your screen for a great shot of the water flowing perfectly.

Interestingly, that nineteen ninety renovation was mostly funded by neighboring businesses who formed a non-profit group to save the landmark. A huge chunk of that money, two hundred and sixty-four thousand dollars to be exact, came from the charitable foundation of Donald Trump. The incredibly generous donation raised a few eyebrows around town, primarily because a beautifully restored fountain indirectly benefited his own Plaza Hotel, which stands just across the street.

This rushing water and striking bronze goddess create a truly iconic New York vignette. Enjoy the refreshing sound of the cascading water, and whenever you are ready, let us cross over to our next location.

Here we are at Grand Army Plaza, specifically the northern half. Right in front of you is a dazzling, twenty-three point five karat gold monument. That is Union Army General William Tecumseh Sherman atop his horse, accompanied by the winged Greek goddess Nike, a striking symbol of victory.

The sculptor, Augustus Saint-Gaudens, unveiled this glittering masterpiece in nineteen oh three. Over the years, the statue has attracted plenty of commentary, including a bit of dark humor. During World War Two, a story went around about a Southern soldier who looked up at the gilded general and his female guide, shook his head, and muttered that he was a typical Yankee, since he rides the horse and makes the woman walk.

But that woman walking ahead of the general holds a fascinating story of her own. If you check your screen, you can see a close-up of her face. Her name was Hettie Anderson, an African-American model from South Carolina. Saint-Gaudens considered her the most striking model he had ever worked with. Tragically, Saint-Gaudens' son Homer later scrubbed Hettie's name and bust from his father's official catalog. Historians point to racial prejudice as the reason for this attempt to erase her from history, though today, her contribution is rightfully celebrated.

The statue has had quite an eventful life. In nineteen fourteen, crews excavating the new subway lines underneath the plaza had to temporarily relocate the fifteen-ton bronze monument into Central Park. The local press had a field day with the sight. The Brooklyn Standard Union gleefully noted that it was the very first time General Sherman ever retreated. In nineteen ninety, a private foundation paid over one hundred and sixteen thousand dollars, or roughly two hundred and eighty thousand dollars today, just to refresh the statue's gold leaf.

Speaking of Brooklyn, this plaza is locked in a delightfully surreal rivalry with a completely different Grand Army Plaza located over in the borough of Brooklyn. The conflict is known as the Menorah War. Every Hanukkah, workers bring in a cherry picker to light a massive, four-thousand-pound steel menorah right here. A menorah is a multi-branched candelabra used in Jewish rituals. For years, both Manhattan and Brooklyn claimed to host the World's Largest Menorah. Even though the Brooklyn candelabra is technically six inches taller, a rabbinical court officially ruled in twenty sixteen that Manhattan holds the true title because they used the branding first. They legally ordered the Brooklyn organizers to call theirs the Central Menorah of Brooklyn instead.

This plaza really captures the heart of the city, blending high-society glamour with a bit of local drama. Whenever you are ready to keep exploring, we can stroll over to our final destination just across the way.

Well folks, we have reached the grand finale. Standing right here, looking at those elegant white brick walls and that green tiled mansard roof, which is the French-style sloping roof up top, you are facing the undisputed king of New York hospitality, The Plaza Hotel.

Take a peek at your app to see how more than a century of development has risen around the timeless French Renaissance-style facade of the Plaza Hotel, transforming the quiet carriage-filled streets of nineteen oh eight into the bustling modern metropolis of today. The Plaza opened its doors in nineteen oh seven with a staggering price tag of twelve and a half million dollars, which is roughly four hundred million dollars today. And from day one, it was a magnet for scandal and spectacle. Just weeks after it opened, the British actress Missus Patrick Campbell caused an absolute uproar by doing the unthinkable. She lit a perfumed Egyptian cigarette in the dining room. When the headwaiter demanded she put it out, because women smoking in public was a severe etiquette breach at the time, she shot back, my good man, I understand this is a free country. I shall do nothing to change it. Management eventually compromised by putting privacy screens around her table.

The Plaza was also home to some incredibly eccentric full-time residents. Take Princess Vilma Lwoff-Parlaghy, a Hungarian painter who moved into a fourteen-room suite in nineteen oh nine. She brought along a massive entourage and a pet lion cub named Goldfleck, who mostly lived in her oversized bathtub.

Over the years, ownership changed hands multiple times. When Donald Trump bought the property in nineteen eighty-eight, his wife Ivana ran it with a famous iron fist, insisting every lemon wedge be cut to precise specifications. But Trump met his match in Fannie Lowenstein, an elderly widow living in a rent-controlled suite for just five hundred dollars a month. Known to the staff as the Eloise from Hell, Fannie constantly called city inspectors complaining that indoor air pollution was shrinking her curtains. Trump finally negotiated peace by giving her a massive suite, new furniture, and a free personal maid for life.

The hotel has also seen its share of history-making protests. Check out your screen for a look at the heavy wood doors of the Oak Room. In nineteen sixty-nine, feminist icon Betty Friedan and other members of the National Organization for Women staged a sit-in there to protest the hotel's men-only lunch policy. Waiters actually physically lifted the table away, leaving the women sitting in an empty circle on the floor until the stock exchange closed at three PM. The terrible publicity forced the hotel to drop the policy four months later.

As we wrap up our tour right here, just steps from where author F. Scott Fitzgerald and his wife Zelda once supposedly took a midnight swim in the Pulitzer Fountain, take a long look at this beautiful chateau. Thank you for walking the streets of Midtown East with me. It has been a true pleasure sharing these spectacular New York stories with you.