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The area was named Madison Square 1814, during president James Madison's term, though Madison Square Park was opened in 1847; the current layout dates to 1870. It was the center of NY society in the 1860s. The park features in O. Henry short stories "Cop and the Anthem" and "Madison Square Arabian Night". Author Herman Melville used to walk here regularly with his granddaughter.

The Star of Hope was erected in 1916 to commemorate the site of the first U.S. community Christmas tree, put up here in 1912. Madison Square Park hosted the nation's first public tree lighting in hopes that the ceremony would become a location where the rich and poor could gather. Traditions came and went over the years but one thing is certain, the public tree lighting remains an American symbol of holiday cheer and goodwill.

The concept of a community "Tree of Light" was a European-inspired idea reportedly launched in 1911 by Upper West Side resident Emilie D. Lee Herreshoff, a socialite and the wife of prominent chemical scientist and yachtsman J.B. Francis Herreshoff. She had proposed the plan to then Mayor William Jay Gaynor, according to Richard W. O'Donnell's 2012 article "The Lighting of the First Community Tree" published in Arbor News by the Cassity Tree Service. Herreshoff's initial request was denied, but later granted in 1912.

It was that Christmas Eve, noted O'Donnell, that Herreshoff flicked the switch and made history when "a faint glow appeared at the very top of the tree, expanding and increasing in intensity until a 10-inch star gleamed brightly against the deep, dark blue of the night sky." After that, "many-colored fire leaped along one show laden branch after another in a blaze of green, blue, white and red lights."

The tree would go on to be a beloved topic of coverage throughout the decades. On Christmas Day 1920, The New York Times described the then 65-foot tree, which featured 5,000 electric candles, as "big enough for the heart of Manhattan" and "could be seen for more than two miles along the highways converging at the park."

The 1942 Christmas season, according to published reports, was under "strict wartime dimout regulations" because the nation's coastal businesses and residences were asked to turn off their lights one half hour after sunset to avoid possible enemy air attacks during World War II. But for the Madison Square Park area, the lack of light didn't keep visitors away from singing carols and celebrating the season around the downsized tree.

Flatiron's ties to baseball can be traced back to 1845 when game changer Alexander Joy Cartwright and his amateur team known as the Knickerbocker Base Ball Club brought a new set of rules to play their game at a vacant lot on 27th Street.

Credited as the "father of modern baseball," Cartwright established the nine-inning game, diamond playing field, and 20 designated regulations that are still used today. They include that all disputes and differences relative to the game, to be decided by the umpire, from which there is no appeal; members must strictly observe the time agreed upon for exercise, and be punctual in their attendance; and a ball knocked outside the range of the first or third base is foul.

Sixty years after his death, Cartwright's contributions to the sport were acknowledged by Congress and he was declared the inventor of the modern game of baseball in 1953. Also posthumously, Cartwright was inaugurated into the National Baseball Hall of Fame and Museum in 1938 in Cooperstown, New York with a bronze plaque that reads: "Alexander Joy Cartwright, Jr. 'Father of Modern Baseball.' Set Bases 90 Feet Apart. Established 9 Innings as a Game and 9 Players as Team. Organized the Knickerbocker Baseball Club of N.Y. in 1845. Carried Baseball to Pacific Coast and Hawaii in Pioneer Days."

The New York Life Building is a 1928 building by Cass Gilbert, the designer of the Woolworth Tower; the rooftop pyramid is a trademark of his. Built on site of New York, New Haven & Hartford Depot, which in 1871 became P.T. Barnum's Hippodrome, later Gilmore's Garden, which the Vanderbilt family turned into the original Madison Square Garden.

This was torn down and rebuilt in 1890 to a design by Stanford White and is considered his masterwork. Topped by Augustus Saint-Gaudens' Diana (now in Philadelphia Museum of Art; a smaller copy is at the Met). In 1906, White was shot and killed in his building's Roof Garden by Harry K. Thaw, jealous husband of White's former mistress Evelyn Nesbit.

In 1900, the Garden was the site of the first U.S. auto show. In 1913, it hosted the Patterson Strike Pageant, organized by Mabel Dodge and Big Bill Haywood, directed by John Reed with scenery painted by John Sloan. The longest Democratic convention in history was held here in 1924, selecting John Davis after 17 days.