City Hall and City Hall Park were completed in 1811 and designed by architects John McComb, Jr. and Joseph Francois Mangin. It is the oldest city hall in the country that still houses its original government functions. Both the interior and exterior of City Hall are designated New York City landmarks. It is home to numerous important artifacts and paintings, including John Turnbull's 1805 portrait of Alexander Hamilton and George Washington's desk.

The Woolworth building was designed by renowned architect Cass Gilbert and commissioned by F.W. Woolworth to be the headquarters for the Woolworth Company. The Gothic Revival structure is one of the earliest U.S. skyscrapers and was the tallest building in the country on its opening in 1913

Built in 1766, St. Paul’s is the oldest church building in Manhattan. In 2001, despite its proximity to the WTC site, the chapel survived the towers’ collapse intact, without so much as a broken window. In the subsequent weeks, it served as a place of rest for first responders while its iron fence became the site of ad hoc memorial displays.

The Corbin Building is a rare surviving example of late 19th-century commercial architecture. While hardly qualifying as a skyscraper today, at nine stories the building towered over its neighbors in 1889.

This 38-story building replaced an earlier Equitable Life Building which was lost to a devastating fire in 1912. Though never the tallest, for a time, this building was the largest building in the world with 1,200,000 square feet of rentable office space.

This is the third Trinity Church. Consecrated in 1843 it was Richard Upjohn's first New York church commission. The adjacent churchyard is the burial site of many famous New Yorkers including Alexander Hamilton and the Schuyler sisters. During the September 11 attacks, the church was used as a refuge from the massive debris cloud created by the collapsed towers.

The New York Stock Exchange at 11 Wall Street was built between 1901 and 1903 by architect George B. Post in the neo-Classical style. Its temple-like facade and pedimental relief sculpture entitled "Integrity Protecting the Works of Man," is meant to represent the strength and security of the country's financial center.

This location was briefly the first Capitol of the United States in 1789. The original 1703 building here was demolished circa 1812. This temple-front structure was completed in 1842.

This magnificent building was one of the first to be erected on Hanover Square after the disastrous fire of 1835. Once occupied by the Hanover Bank and the New York Cotton Exchange, it is now a private club.

Fraunces Tavern was built in 1719 originally as a mansion and was converted into a tavern in 1762. In December of 1783 it was the site of General George Washington’s farewell meeting with his officers.

Designed by Cass Gilbert, this ornate Beaux-Arts building was constructed between 1900 and 1907. Interestingly, it was designed to face the historically significant Bowling Green and not the harbor (whereas most other customs buildings faced the water).

Castle Clinton is a sandstone fort built in 1811 during the re-fortification of New York Harbor before the outbreak of the War of 1812. It was given its name in 1815 after the then Mayor DeWitt Clinton. It has served a variety of purposes including the city's first immigration processing center and later its first aquarium.