Madison Square, located in the Flatiron district, is one of the historically most important squares in New York City. The attractive 19th century Madison Square Park is surrounded by historic landmarks from the Gilded Age, including the famous Flatiron building and the classical Metlife tower.

The first decades after Madison Square Park was officially designed as a public space in 1847, Madison Square was mostly a residential area. From 1859 onwards, with the opening of the Fifth Avenue Hotel, the area started to become the center of New York's social life. Many major hotels moved into the area, followed by retailers and the entertainment industry. At the turn of the 19th century, Madison square had become a prime office location and Manhattan's shopping paradise. Such was the concentration of shops that the section of Broadway between Union Square and Madison Square became known as the Ladies' Mile. Most of the retailers have long moved up town, but many of the buildings in the area have been preserved.

During its heyday at the beginning of the 20th century, Madison square became a prime office location.
The most famous building in the district, the Flatiron Building, was constructed in 1902 by the famous Chicago architect Daniel Burnham in the then popular Beaux-Arts style. Initially named Fuller building after the construction company that originally occupied the building, the 21 story building was soon dubbed Flatiron because its triangular shape resembles that of a flat iron. Its shape and height made the Flatiron one of New York's most recognized landmarks.
In 1909, the Metlife Tower was constructed near Madison Square park as the new headquarters of the Metropolitan Life Insurance Company. It was added to the original 1893 headquarters. The 700ft, 51 stories tall building was modeled on the campanile at St. Mark's Square in Venice. When constructed, it was the tallest building in the world. It would keep that title until the completion of the Woolworth Building in 1913.
Next to the Metlife tower, across 24th street, is another Metropolitan Life Insurance building, known as the 'north building'. This art deco building was designed to be an immense 100 story tall tower. This tower would hand the title of the world's tallest building back to the Metropolitan Life Insurance Company, but the Great Depression made an abrupt end to these plans: only the 29 first floors were built before construction was halted in 1932.
Another imposing building near Madison Square is the New York Life Insurance Company building. It was erected in 1928 at the site of the original Madison Square Garden. The NY Life Insurance Company building is known for its octagonal gilded spire. Its design by Cass Gilbert (architect of the Woolworth Building) was inspired by the Salisbury Cathedral in England.

The Madison Square park is bordered by Fifth and Madison Avenues and 23rd and 26th street. Since its rededication in 2001 this park is once again one of the most enjoyable parks in Manhattan. From anywhere in the park you have a great view on the surrounding architectural landmarks.
The park is littered with mostly 19th century statues. At the southeast corner of the park is a statue of Senator Roscoe Conkling, who froze to death during the great 1888 blizzard. At the north end of Madison Square park is a 1880 statue, designed by Augustus Saint-Gaudens. It depicts the Civil War admiral David Farragut.
Between 1876 and 1882, the right arm and torch of the Statue of Liberty were on display in the park, in order to raise money for the construction of the statue.


Madison Square was also the location of the original Madison Square Gardens. Madison Square would soon be associated with these temples of entertainment. The first one opened in 1879 at the northeast corner of Madison Avenue and 26th street. This was were most of the famous fights of boxing legend Jack Dempsey took place. The second Madison Square Garden, replacing the first one in 1889 was designed by Stanford White. It featured a concert hall, theater, concert hall and roof garden. The building had a prominent tower built after the Giralda tower in Sevilla, topped by a nude statue of of the goddess Diana. In 1925 the building was demolished and the Madison Square garden moved to 8th Avenue and 49th streets. The current Madison Square garden is located at Penn Station. (between 31st and 33rd streets, 7th and 8th avenues)