The airship mast on top of New York's most iconic skyscraper secured its position as the world's tallest building at the time of completion.

Herald Square is named for a newspaper known for sensational coverage of scandal and crime.

Macy’s claims to be the first department store in New York City to put on a holiday window display.

The original Penn Station was built in 1912 and required the demolition of 500 buildings and the digging of tunnels under the East and Hudson Rivers. Its 1963 demolition became a rallying cry for the nascent preservation movement in America.

The main United States Postal Service Building bears the inscription: "Neither snow nor rain nor heat nor gloom of night stays these couriers from the swift completion of their appointed rounds."

Opened as a hotel in 1872, Gilsey House's crowning architectural feature is its extraordinary three-story mansard roof!

Famed WPA photographer Berenice Abbott captured the ornate interior and facade of this 19th century theatre a few months before it was demolished in 1939.

Madison Square Park is a seven-acre urban park. Since 2004, it has hosted the—often monumental— works of more than 30 artists.

Nicknamed "Flatiron" for its shape, the Fuller Building was first derided as a misshapen symbol of commercial greed and later extolled as an exhilarating symbol of modernity.

A precursor to the modern sightseeing bus. Look how happy they are!

Before the tower's completion, a large light was placed on the top to display the results of the presidential election of 1908, visible for miles around.

Completed in 1899, 25% of the cost of this courthouse building was spent on sculpture!

Baruch College began as part of the 1847-founded Free Academy, which aimed to provide education to New Yorkers who could not afford to enroll in the city's private colleges.

This space is best known for hosting the International Exhibition of Modern Art in 1913; the “Armory Show” was the first presentation of Modern art in the United States.

This is one of two private parks in New York City. Only residents of the buildings surrounding the park who pay an annual fee of $350 are given a key.