From 19th-Century circuses and swanky hotels to an art and foodie destination today, this 6.2-acre green space continues to represent a city that is constantly reinventing itself.

Lately, Madison Square Park has provided a staging area for provocative art installations, pop-up food courts and outdoor work spaces. Perhaps what most people know it for, however, is as the site of the original Shake Shack.

But within this 6.2-acre Manhattan green space, bordered by Madison and Fifth Avenues, Broadway, and 23rd and 26th Streets, there are layers of history that for decades made the park the cultural center of the city.

During its “golden age,” from around 1870 to 1910, Madison Square Park was the anchor for the classiest hotels and restaurants in New York. It was also the possible birthplace of baseball; the park where Theodore Roosevelt and Edith Wharton grew up, and where Herman Melville, Mark Twain and O. Henry often strolled; the site of not one but two circuses featuring exotic animals, chariot races and gladiators; and the scene of one of the most talked-about scandals in the city’s history — the murder of the architect Stanford White by the jealous husband of Evelyn Nesbit, the showgirl and model for the original “Gibson girl.”

The Flatiron Building, completed in 1902, anchors Madison Square Park to the south. Detroit Publishing Company, via Library of Congress

Even now, if you sit on a bench and peer through the trees amid the hustle of office workers cutting through the park or young families making their way to the crowded playground, you can almost picture the surrounding rows of brownstones whose color, as Edith Wharton crankily observed in “The Age of Innocence,” “coated New York like a cold chocolate sauce.”

These few blocks contain vital New York history, from an early city planner envisioning Manhattan’s future grid, to men of the cloth clashing with saloon owners amid the area’s rampant development (and accompanying corruption) in the 19th century, to architectural feats that both paid off (the Flatiron building) and failed to survive the wrecking ball (the first two iterations of Madison Square Garden).

The rapid, sometimes reckless changes that the area has gone through — from uninhabitable hinterland to coveted real estate that served as home to one dynamic phase of New York history after another — are a microcosm of what New Yorkers love and hate about their city.

1686 Swampland

One of the early buildings in Madison Square Park was a home for juvenile delinquents. It relocated to Randall’s Island in 1854. George Hayward, via New York Public Library

The plot of land that eventually became Madison Square Park was hardly the best that Manhattan had to offer — swampy, sandy soil crossed from west to east by Cedar Creek, later called Madison Stream. In 1686 it was designated public land and used in quick succession as a hunting ground, a potter’s field, a parade ground, an arsenal and a home for juvenile delinquents.

1800 to 1850 A City Expands

In the 1830s, the area around Madison Square was considered so remote that Corporal Thompson’s Roadhouse (also known as Madison Cottage) at 23rd Street, the last stop for stagecoaches to and from the city, was still open for business. Above, an 1850 cattle show at the Roadhouse. Guy Loring, via Museum of the City of New York

Manhattan’s grid plan may have originated on the banks of Cedar Creek, said Miriam Berman, author of “Madison Square: The Park and its Celebrated Landmarks.” One afternoon in 1810, so the story goes, members of the Commission on Streets and Roads were wandering around discussing possible street designs for burgeoning New York. They’d already rejected a plan to preserve the island’s natural contours as well as the square block layout that Philadelphia had adopted. One of the commissioners saw the sun casting a rectangular shadow through a workman’s sand-sifting screen — and the blueprint for Manhattan’s wide avenues and narrow cross-streets was born.

Some 20 years later, the area around Madison Square was still considered so remote that Corporal Thompson’s Roadhouse (also known as Madison Cottage) at 23rd Street, the last stop for stagecoaches to and from the city, was still open for business. Guests were subject to rules on illustrated placards like “No more than five people to sleep in one bed,” according to the book “Incredible New York: High Life and Low Life of the Last 100 years” by Lloyd Morris.

Origins of the Great Pastime

The Knickerbocker Base Ball Club, also pictured with members of the Brooklyn Excelsior Base Ball Club, in 1858. In 1842 the Knickerbockers started playing near what is now known as Madison Square Park, but moved to Hoboken, N.J., a few years later. via New York Public Library

Historians have largely discredited the legend that Abner Doubleday fathered the modern version of baseball in Cooperstown, N.Y., and now think that one of its likely birthplaces was New York City. Around 1842 a group of young businessmen and medical students took the air on a sandlot at what later would be 27th Street and Madison Avenue. Playing a variation of several English ball games including “rounders,” they formed a team with the fancy name “Knickerbocker Base Ball Club,” after the original Dutch settlers. Their leader, Alexander Cartwright, helped codify the rules into something that resembled modern baseball — though balls caught on one bounce were considered an out, and only underhand pitching was allowed. When the sandlot fell victim to developers, the Knickerbockers moved to Hoboken, N.J., where in 1846 they lost the first recorded game of baseball against a rival team, the New York Nine, 23-1.

1850 to 1900 Boom Town

A view from 1896 of Fifth Avenue at 26th Street, showing Delmonico’s Restaurant. Byron Company, via Museum of the City of New York

Following the official opening of Madison Square Park in 1847, prolific development began in the area. The soft sandstone used in the hundreds of brownstones that shot up in the mid-1850s came from New Jersey and Connecticut. Compared with the genteel dwellings to the south on Washington Square, these new rowhouses were crowded and dark, and according to architectural historians like Lewis Mumford in “The Brown Decades” (1931), there was an uninspired sameness to the designs. The buildings were narrower than their predecessors, he wrote, with small, cluttered rooms.

Nonetheless, high-end shops and top restaurants like Delmonico’s were soon sprouting up along Broadway and Fifth Avenue, and private clubs like the Union, Athenaeum and Lotos had opened nearby. But according to the book “Gotham: A History of New York City to 1898,” dozens of “concert-saloons” also appeared — raunchy predecessors of Playboy-like clubs where “waiter girls” in short skirts and high red boots with tassels joined patrons for drinks and music-hall entertainment before they retired to private rooms or nearby brothels. Ms. Berman claims that at the Louvre, perhaps the most elegant concert-saloon in Madison Square, “one who found oneself in a transient or disconnected state could cultivate the art of real pleasure.”

Disguised in dirty clothes, with his mustache lathered with soap, the Rev. Dr. Charles H. Parkhurst, pastor of the Madison Square Presbyterian Church, led a group of detectives to collect evidence of the “rottenness” festering in some 254 saloons. Hulton Archive, via Getty Images

The seamy aspect emerging around the park so angered the Rev. Dr. Charles H. Parkhurst, pastor of the prestigious Madison Square Presbyterian Church, that in 1892 he denounced from his pulpit the city’s moral corruption. Disguised in dirty clothes, his mustache lathered with laundry soap, Parkhurst led a group of detectives to collect evidence of the “rottenness” festering in some 254 saloons around the city. A group of grateful citizens suggested that the city be renamed “Parkhurst.”

And then there were the circuses.

Opening night (1853) at Franconi’s Hippodrome, which had seating for 10,000 spectators. via New York Public Library

In 1852, Corporal Thompson’s Roadhouse was finally torn down and replaced by Franconi’s Hippodrome, a large arena with seating for 10,000 spectators. It featured elephants and camels as well as chariot races around its 40-foot wide track. But the Hippodrome lost money, and closed after two seasons. Twenty years later, P.T. Barnum installed his Monster Classical and Geological Hippodrome on the northeast corner of the park in and around the train sheds that used to be part of the old New York and Harlem Railway depot. By 1880 the train sheds’ owner, William K. Vanderbilt (grandson of the famous Commodore), renovated and renamed the area Madison Square Garden.

To the usual circus acts, Barnum added curiosities from his downtown “museum” as well as tattooed men and cowboys and Indians. When the circus wasn’t in town, Vanderbilt booked six-day bicycle races, horse and dog shows, as well as “illustrated lectures on pugilism” (boxing had been outlawed in 1856), including a John L. Sullivan and Tug Wilson four-rounder that turned away 10,000 fans, according to Ms. Berman. But Barnum’s circus didn’t make money either, and after the circus attracted only a few hundred spectators during the blizzard of 1888, he closed up shop. He died before bringing the circus back into the new, expanded Garden that opened on the same site in 1890.

The first Madison Square Garden, circa 1879-1890. Geo. P. Hall & Son/The New York Historical Society, via Getty Images

Though the west side of the park was shaved down in 1870 to widen Broadway and make room for hansom cab parking, it was redesigned with fountains and winding paths by William Grant and Ignatz Pilat, one of Frederick Law Olmsted’s associates; since then, the park has stayed more or less true to Grant and Pilat’s design.

Statues Emerge

As the place to be in the latter part of the 19th century, Madison Square had its share of characters.

Roscoe Conkling, the Republican powerbroker and U.S. senator, was described by a Navy secretary as an “egotistical coxcomb.” His demise after the blizzard of 1888 has become part of the square’s history. Hulton Archive/Getty Images

Take Roscoe Conkling, the Republican power broker and U.S. senator. A self-styled dandy, Conkling wore a “formal black cutaway coat,” wrote Scott S. Greenberger in “The Unexpected President: The Life and Times of Chester A. Arthur” (Conkling had been an associate of Arthur before Arthur became president). “He usually complemented it with a light-colored vest and trousers, a vivid red or blue bow tie, and English gaiters buttoned over his freshly polished, pointed shoes.” Gideon Wells, a Navy secretary of the time, described Conkling as an “egotistical coxcomb.”

Conkling’s demise has become part of the square’s history.

Digging out after a major 19th-century snowstorm. via New York Public Library

Leaving his Wall Street office as the blizzard of 1888 closed in, Conkling hailed a hansom cab whose driver wanted $50 for the trip uptown; he rejected the offer with his usual colorful language. He was 58 and a skilled amateur boxer, and decided to walk the three miles to his suite of rooms on Madison Square.

But the blizzard that dumped 40 inches of snow onto the city in 36 hours was too much even for Conkling. Hours after he’d started, he collapsed in sight of his private club — and he died some weeks later. Though political allies petitioned to put his statue in Union Square, the parks department determined that he wasn’t of the same stature as Washington and Lincoln, who were already memorialized there. His supporters did manage, however, to convince the department to put his statue, which was dedicated in 1893, in the southeast corner of Madison Square Park, near where he fell.

The lantern of the Statue of Liberty was on display in Madison Square Park between 1876 and 1882 to raise money for its completion. via Museum of the City of New York

Although many sculptures have come and gone from the park (like the torch-bearing arm of the Statue of Liberty that for six years was on display there to raise money for its completion), other notable works remain.

There is the obelisk-topped tomb of William Jenkins Worth, a general during the Seminole and Mexican Wars, which can be found at the junction of Broadway and Fifth at 25th Street. Installed in 1857, apart from Grant’s Tomb it is the only monument-mausoleum in the city.

William Henry Seward, secretary of State under Lincoln and Johnson, who engineered the 1867 Alaska Purchase, has loomed large in bronze at Fifth Avenue and 23rd Street since 1876. A rumor persists that the sculptor, Randolph Rogers, tried to stay within his budget by placing Seward’s head on a seated bronze casting of Abraham Lincoln.

A memorial to Admiral David Glasgow Farragut (the Civil War naval hero of “Damn the torpedoes; full speed ahead!” fame), was dedicated in 1881. Created by two stars of the era, Stanford White and the sculptor Augustus Saint-Gaudens, who later created the nude Diana to sit atop the tower of the White-designed Madison Square Garden, the statue and beautiful bas-relief base can be found near Fifth Avenue and 26th Street.

Ghosts of Hotels and Arenas Past

Interior of the Fifth Avenue Hotel, circa 1895. Regulars there included Mark Twain and Edwin Booth. via Museum of the City of New York

Three major buildings — one still standing, two long gone — distinguished Madison Square in its heyday.

The Fifth Avenue Hotel, built in 1859, was such a gamble by owner Amos F. Eno that it was nicknamed “Eno’s Folly.” The skeptics were wrong. With 600 rooms and the first hotel passenger elevator in the United States, it became a political, artistic and financial mecca. Regulars included magnates like Jay Gould and Jim Fisk and artistic types like Mark Twain and the actor Edwin Booth. Every president from James Buchanan (1857-1861) to William McKinley (1897-1901) stayed there when they were in town.

“The Amen Corner” at the Fifth Avenue Hotel was popular among politicians. Brown Brothers, via Museum of the City of New York

The hotel was famous for its “Amen Corner,” a bench in the hotel’s lobby where Republican politicians plotted strategy. Theodore Roosevelt, who grew up in a brownstone at 28 East 20th Street, established headquarters in the hotel for both his unsuccessful bid for mayor (1886) and successful run for governor (1898), according to Ms. Berman.

On the night the hotel closed in 1908, it was said, loyal patrons of the bar shelled out the huge sum of $7,000 for their last drinks.

Stanford White designed the second Madison Square Garden, a Moorish-Venetian-Renaissance-style building. Frank M. Ingalls/The New York Historical Society, via Getty Images

The second iteration of Madison Square Garden was a Moorish-Venetian-Renaissance-style building designed by Stanford White in 1890. In addition to the main arena that seated thousands of spectators, there was a theater, a concert hall, a shopping arcade and a rooftop garden.

White reserved several floors for himself in the adjoining tower, and it was there or nearby that he seduced the young showgirl Evelyn Nesbit. For a time White supported Nesbit and her mother in exchange for her willingness to play around and relax, bejeweled and nearly nude, on a red velvet swing.

The 1913 National Horse Show at Madison Square Garden. Bain News Service, via Library of Congress

At the age of 20, she married the multimillionaire Harry Thaw, who had been harboring a grudge against White for years. On June 25, 1906, Thaw took out a revolver and shot White on the rooftop of the Garden, thus setting the stage for the Trial of the Century.

Though Nesbit’s testimony at the trial saved Thaw from the gallows — he got off on an insanity plea — she never quite got over White, calling him “the most wonderful man I ever knew.”

A portrait, circa 1900, of Evelyn Nesbit, who became part of the so-called Trial of the Century when her husband, Harry Thaw, murdered the architect Stanford White, her former lover, on the rooftop of Madison Square Garden, which White had designed. Gertrude Käsebier, via Library of Congress

As for the scandalous jaunts that took place in White’s tower, which were brought up during the murder trial and to the press: “Don’t forget I was only 15,” Ms. Nesbit said, “and I enjoyed swinging.”

Years later, E.L. Doctorow wrote about the White assassination and made Evelyn Nesbit one of the central characters in the 1975 novel “Ragtime.”

1900 to 1918 A ‘Monstrosity’ Is Erected, and the Exodus Begins

The Flatiron Building initially received mixed reviews. The New York Tribune called it “a stingy piece of pie” and The Times described it as “a monstrosity,” while the photographer Alfred Stieglitz regarded it as “a picture of a new America in the making.” Detroit Publishing Company, via Library of Congress

Of all the impressive buildings near the square, there is nothing quite like the steel-frame Flatiron Building on 23rd Street. Instantly popular with the public when it was completed in 1902, the building initially received mixed reviews from critics. The New York Tribune called it “a stingy piece of pie” and The Times described it as “a monstrosity,” while the photographer Alfred Stieglitz regarded it as “a picture of a new America in the making.”

Construction in the early 1900s of the MetLife Tower. H.C. White Company, via Library of Congress

By World War I, much of the action had moved uptown. Grand mansions filled upper Fifth Avenue, and Madison Square started to lose its luster. It became a commercial center, with two insurance companies — New York Life and MetLife — building skyscrapers on the sites of beloved Stanford White buildings, the Garden and Madison Square Presbyterian Church. (According to Ms. Berman’s book, a critic of the time bemoaned the razing of the church, which combined Corinthian columns with a dome inspired by Istanbul’s Hagia Sofia, saying that it “took five thousand years to achieve … and they demolished it in a week.”)

1918 to 2018 Toys, Science, Art, Burgers

Madison Square Park, today, with the MetLife Tower, center left. Karsten Moran for The New York Times

With the flight of the moneyed classes, the area became known for clothing manufacturers, then for toys. In 1926 the Lionel company displayed its first model train layout in its Madison Square headquarters, and in 1941, A.C. Gilbert, inventor of the Erector Set, opened his Hall of Science, which featured American Flyer model trains; Lionel acquired its longtime rival in 1967. The building at 200 Fifth Avenue that replaced the Fifth Avenue Hotel housed a number of toy manufacturers, and eventually became the International Toy Center; the New York Toy Fair was based there for years, but was sold in 2005. Now the building is once again a destination; it is the home to the Italian food emporium Eataly NYC.

There were a few other notable additions to the area in the 20th century. Eisenberg’s Sandwich Shop at 174 Fifth Avenue near 22nd Street bills itself as “raising New York’s cholesterol since 1929.” It may be the oldest surviving diner in the city. In 1990 Harriet Feigenbaum’s stark memorial to the victims of the Holocaust — an aerial view of Auschwitz — was added to the side wall of the Appellate Division of the New York State Supreme Court building at 25th Street and Madison Avenue. (The building also houses a large collection of turn-of-the-century American art.)

By the late 20th century, some buildings around Madison Square stood half-empty, and the park itself had lost its appeal. A major restoration, especially of the southern end, was initiated in 1997 by a precursor of the Madison Square Park Conservancy, which in turn brought about a revitalization of the neighborhood.

Perhaps most importantly, the restaurateur Danny Meyer suggested adding a hot-dog stand (using the kitchen of Eleven Madison Park down the street) to the park in 2000. The venture became so popular that four years later it was given a permanent home there — the first of over 100 Shake Shacks around the world.

“Our partnership has continued to grow, and Danny’s vision and food have been integral to making Madison Square Park what it is today,” said Keats Myer, the executive director of the Madison Square Park Conservancy.

Nowadays luxury condos overlook a well-maintained park complete with art exhibitions, concerts and a projected 60-year “tree succession plan” that includes planting species native to Manhattan when Henry Hudson set foot on the island.

A major restoration, especially of the southern end, was initiated in 1997 by a precursor of the Madison Square Park Conservancy, which in turn brought about a revitalization of the neighborhood. Karsten Moran for The New York Times

Only faint vestiges of the park’s golden age remain. The facade of the upper two stories at 14 East 23rd Street is literally the only visible sign of the brownstones that once fronted three sides of the square.

When native New Yorker Martin Scorsese needed a setting that looked like 1870s Madison Square for his film adaptation of “The Age of Innocence,” he had to travel to Troy, N.Y., to find period-appropriate brownstones that had yet to meet the wrecking ball.