Square to Square History Walk through the City

Square to Square History Walk through the City



New York, NY / Culture / Good for Kids / Sights

The squares throughout New York City, from the parks like Madison to the shopping stops like Times, are filled with cultural reference points, grand architecture, and changes that span centuries. On this tour, we will take a look at the squares through the lens of the 1900s.

Photo: Library of Congress Prints and Photographs Division

1. Walk Under Washington Square’s Arch

Washington Square Park

1 5th Ave New York, NY, 10003

Get Directions

The city acquired this parcel of land in 1797 and converted it from farmland into a potter’s field, or burial ground for unknown people and the poor. While the record books state otherwise, there is a belief that public executions were once held here, specifically in an elm tree called the Hangman’s Elm. However, in 1825, the burial ground was shut down, and, a year later, it was converted into a training plot for voluntary militia called the Washington Military Parade Ground. It became a public park the following year.

The marble arch that stands there today is actually a replacement built between 1890 and 1892 for a wooden one. The original arch was built in 1889 and was a celebration to the centennial of George Washington’s presidential inauguration.

Designed by architect Stanford White, the marble arch was inspired by the Arc de Triomphe in Paris, and, when they were erecting it in the park, they unearthed bodies and coffins dating back to 1803.

2. See the George Washington Statue from 1870’s

Union Square Park

30 E 14th St New York, NY, 10003

Get Directions

Once another potter’s field, the city took control of the plot in 1833 and opened it as a park in 1839. While believed to be connected to political gatherings, the name is actually related to the “union” of Broadway and 4th avenue, formerly Bloomingdale and Bowery. This was the same corner that once held the George Washington statue, which was moved in 1930 to protect it from pollution and traffic.
This is a short video filmed in 1901 along Broadway at Union Square.

3. Browse the Farmer’s Market of Union Square

Green Market, Union Square

33 Union Square W New York, NY, 10003

Get Directions

Since 1976, fresh produce and homemade goods have been available from local farms and sellers through Union Square’s Greenmarket. Goods can be bought from 8:00 am until 6:00 pm Mondays, Wednesdays, Fridays, and Saturdays.

Due to an excellent layout and location, Union Square has historically been a great place for local merchants to sell their products.

The Greenmarket offers all sorts of goods, such as produce, baked goods, wines and juices.

4. Stop by Eisenberg’s Sandwich Shop for Lunch

Eisenberg Sandwich Shop

174 5th Ave New York, NY, 10010

Get Directions

Serving the community since 1929, Eisenberg’s is an amazing deli known for their pastrami sandwiches and egg cream drinks.

Part of Eisenberg's old charm is that it still offers favorites from a bygone era - like egg creams. Despite the name though, egg creams don’t have any egg or cream in them. They are actually milk, seltzer, and chocolate syrup.

5. Appreciate the Flatiron Wonder of 1902 Today

The Flatiron Building

1 E 23rd St New York, NY, 10010

Get Directions

Once expected to blow over due to its triangular shape, the Flatiron Building has stood mostly unchanged for over a century against an evolving landscape.

Daniel Burnham, the building’s architect, designed it of Renaissance architecture with Beaux-Arts styling.

6. Check Out the Many Faces of Madison Square Park

Madison Square Park

Madison Ave New York, NY, 10010

Get Directions

Madison Square Park, like some of the other parks mentioned, was previously a potter’s field. Madison Square’s use as a potter’s field was replaced by Washington Square in 1797. By 1811, the 240 acres from 23rd to 34th and 3rd to 7th was being used for a US Army arsenal as well as a military parade ground, or volunteer militia, named after James Madison. When the arsenal was no longer used, the “House of Refuge” was established in 1825 to care for juvenile delinquents until a fire destroyed the building in 1939. After some renovation, the park was eventually opened with heavily adjusted borders in 1947.

7. Check Out the Old Site of Madison Square Garden I & II

The New York Life Insurance Building

51 Madison Ave New York, NY, 10010

Get Directions


8. Enjoy Herald Square’s Journalistic History

Herald Square

19 W 31st St New York, NY, 10001

Get Directions

Herald Square is less a square and more two triangles created from an intersection united by Broadway, 33rd, and 6th. The northern triangle is named after the New York Herald, an old newspaper whose headquarters were located in the square while the southern triangle was named Greeley Square for Horace Greeley, the publisher of a rivaling newspaper, the New York Tribune. The two newspapers would eventually merge in 1924 to become the New York Herald Tribune, which would cease publication by 1966.

In Herald Square, the James Gordon Monument stands along 35th St. This mechanical clock was created by Antonin Jean Carles in 1895. It has sculptures of Minerva, the Goddess of Wisdom, a large bell that rings every hour, and bronzed laborers ringing the bell. The clock and sculptures are original pieces from the 1894 New York Herald Building, which was demolished in 1921.
This video was filmed in 1896 at Herald Square.

9. Shop at Macy’s Large Presence


151 W 34th St New York, NY, 10001

Get Directions

In 1902, the Macy’s flagship made its third and final move north to Herald Square. The move had taken them so far north from other stores that the company provided transportation for customers from 14th to 34th. Since 1924, it has been the world’s largest department store and is now 111 years old.

10. Witnesses the Light Shows of Times Square

Times Square

1475 Broadway New York, NY, 10036

Get Directions

This famous section of New York was named Times Square in 1904 after The New York Times moved into the famous skyscraper, One Times Square.

Before its name and image, Times Square was a horse ranch-turned-economic hub known as Longacre Square (1898).

The New York Times celebrated their new building with fireworks on January 1st, 1905 at midnight; a tradition we continue today.

11. Enjoy Dessert with Junior’s

Junior's Cheesecake and Desserts

1515 Broadway New York, NY, 10036

Get Directions

Junior’s may not carry the same historic significance in Manhattan as it does in Brooklyn, but this classic New York restaurant that has a history of serving great food, particularly cheesecakes. This cheesecake, from a recipe the dates back three generations, has a reputation in New York. In 2010, that reputation earned it a spot on Food Network’s Food Feuds in a battle of cheesecakes. Against Eileen’s Special, Michael Symon declared Junior’s the best cheesecake in the city.