The Best, and Most Surprising Vintage Images In American History

In less than 200 years, America has become one of the greatest powerhouses the world has ever seen. Since the days of George Washington crossing the icy Delaware River to help secure our independence, America has gone through drastic changes, probably greater than any other country during the same time period. Urbanization took the United States by storm in the mid 19th Century, with many families and immigrants flocking to big cities on the east coast such as New York, Boston, and Philadelphia. As time went on, more major cities began popping up on the map, such as Miami, Chicago, and Los Angeles, all becoming extremely popular spots. Urbanization only continued to increase through the 20th century, and society is currently in a time where it is difficult to imagine what life must’ve been, and looked like back in the days before we had massive skylines completely lit up at night. This is a gallery so you get a good understanding of what America had to go through to get all of it’s beautiful skylines, and remarkable landmarks.



The Quincy Market has been around for nearly 2 centuries, with it opening in the early 1800’s.

At the time it was one of the largest market complexes in the United States, and is now a National Historic, and Boston Landmark.

New York City

Here we see a picture of the location of the flatiron building in 1850 at the crossing of Broadway and 5th Avenue, prior to it’s opening in 1902. The building was later named the Flatiron for its resemblance to a clothing iron, becoming one of the most iconic buildings in the world.

The whole neighborhood surrounding the building was renamed the Flatiron District, and it being designated as a National Landmark. As you can see, the streets of New York were very different back in the mid 19th century.

Washington D.C.

Here we can see the construction of the Washington Monument back in the 1850’s. The monument began construction in 1848, but from 1854 until 1877 construction was halted due to a variety of reasons such as lack of funds, and the Civil War.

This is a photo of the monument while construction was halted during this 20 year span. The monument was finally completed in 1884, and officially opened in 1888. I’m sure it is hard to imagine that the great Washington Monument once resembled a lighthouse.

New York City

Here we can see the Brooklyn Bridge under construction back in the mid to late 19th century. The bridge began construction in 1869 and was completed in 1883 when it was originally called the New York and Brooklyn Bridge.

The bridge is one of the most well known bridges in the world, and is a national, and New York City landmark. Imagine the amount of traffic there would be in New York without the creation of this incredible bridge.

New York City

This photo of the construction of the Manhattan Bridge was taken in 1909, which is the same year the bridge was open for use. The construction of the bridge was delayed due to lack of funds, and disputes over which materials to use, but was ultimately completed in 1909.

The Manhattan Bridge connects Manhattan and Brooklyn, and works as an essential part of New York City traffic flow. It is located just north of the Brooklyn Bridge in downtown Manhattan.


This is what the city of Chicago looked like before the creation of their famous “L” train. Back in 1909 cable cars were crowding the streets that also included vehicles, horses, and pedestrians.

The creation of the “L” with its elevated, and underground lines, clearly changed the way the city functioned, clearing up the combination of pedestrian, automobile, and cable car traffic.

Washington D.C.

The Lincoln Memorial began construction in 1914 and opened in 1922, with a small delay during construction due to World War I, and a lack of funding.

Since the time of Lincoln’s death nearly 50 years earlier, there had been a public demand for a proper memorial for President Lincoln, with it finally coming to fruition in 1914.


This is the Custom House Tower while under construction in the 1910’s when the tower was being added to the original building that was built in the mid 1800’s.

This view of the tower is seen from Quincy Market, and was officially completed in 1915.


Back in 1916, the Ford Motor Company was running the city of Detroit, and here you can see workers making their way to the factory for work.

Back in the early 20th century, Ford completely controlled the economy of Detroit, and is what got the city into the recession it still deals with today.

Washington D.C.

This picture taken of the back yard of the White House shows a flock of sheep minding their own business. This picture was taken in the early 20th century, when security wasn’t nearly as large of a priority at it is in the modern day.

This is not the way most would picture the White House in the modern day, with it’s high maintenance security a flock of sheep probably wouldn’t even be able to make it to this point.

New York City

This is a photo of the famous Grand Central Station back in 1930, beautifully capturing light beams enter through windows into the main concourse. One of the most well known train stations in the world, Grand Central is known for its grandeur and beauty.

The terminal opened back in 1913, and has provided New Yorker’s, and tourists with beauty unlike any other station, to go along with easy access to all over New York City.

Los Angeles

It may be hard to believe, but the famous Hollywood sign actually used to read Hollywoodland. This was the sign from 1923 when real estate developer H.J. Whitely decided to advertise his new development with a sign.

Developers decided to change the name of the development, to go along with sign, changing the name of the area to Hollywood. They went on to change the sign to reading Hollywood as well in 1949, when the sign was restored.

Washington D.C.

This is a line to enter the White House for an assumed New Years eve celebration. This moment captured is truly incredible, with hundreds of people waiting to celebrate the new year in the President’s home.

Although the White House still holds major events, it is difficult to imagine an event like this occurring in the modern day. It seems like these are random citizens, wanting to celebrate the new year with their president.

Los Angeles

Pictured here is the famous Santa Monica Pier in 1924, with people lined up on the beach, and the boardwalk in the background, which is still up and running today.

The Santa Monica Pier is located close by to the popular Venice Beach, and is well known for its amusement park rides. The pier was actually destroyed back in 1983, and was restored to its modern look.

New York City

Yes, back in the early to mid 20th century, New York had 3 baseball teams. The two stadiums showed here are Yankee Stadium, at the bottom of the picture located in the south Bronx, while the Polo Grounds, home of the Giants, sits opposite the Harlem River in upper Manhattan.

The Giants eventually moved to San Francisco in 1958, while the Yankees have stayed in the same area in the South Bronx, but have moved across the street to a new stadium.


This photo captures the opening of the Ben Franklin Bridge back in 1926. This is quite an interesting way to celebrate the opening of a bridge, you would think driving over it would make much more sense.

The bridge connects Philadelphia with Camden, New Jersey.

New York City

The Empire State Building began construction in 1930, and was completed a little over a year later in 1931. The Empire State Building is known for having been the tallest building in the world from 1930 until 1970.

This is a fabulous photo captured of one of the men who would risk his life everyday to help build the famous building. This also previews the tremendous views that the Empire State Building would have.

Santa Monica

The Pacific Coast Highway runs along the Pacific coastline of California, and is almost 700 miles along, stretching from Los Angeles to north of San Francisco.

This highway is known for its unbelievable views, which can be seen in this photo back in 1930. The highway was still gorgeous even before its full development.

New York City

The George Washington Bridge began construction in 1927 and was completed in 1931, so this photo was taken somewhere in the middle of that time period. This is a wild look back at what is now the busiest bridge in the whole world, connecting New York City with Fort Lee, New Jersey.

The George Washington Bridge is also one of the longest suspension bridges in the United States. Imagine what getting from New York to New Jersey must’ve been like before this amazing and beautiful bridge.

Washington D.C.

This photo was captured in 1926, in the Lincoln Memorial Reflecting Pool, in which the memorial can be spotted in the background.

In today’s world, you don’t really see anyone playing in the Reflecting Pool, but it was probably a hot summer day and these kids needed a pool.


This photo of Miami Beach was taken in 1925, before it was developed by the Collins family. Originally a piece of land no one was interested in populating, it is now one of the most popular beach resorts in the world.

You can see that the island of Miami Beach used to be almost deserted, with their being few beach resorts open in 1925.

New York City

The Brooklyn Dodgers were the third team located in New York City, having played at the historic Ebbets Field. The Dodgers made the decision to move to Los Angeles in 1957 along with the Giants.

The historic stadium was also home to three NFL teams, and was demolished in 1960, being replaced by apartment buildings known to this day as the Ebbets Field Apartments

Washington D.C.

Here we can see just how different the lifestyles of the early 20th century, and the 21st century really are.

Standing in front of the Capital Building, these kids seem ready to hit their paper route, very different than school or camp most kids are forced to attend in the modern day.

San Francisco/ Oakland

This picture captures the construction of the Bay Bridge in 1936. The Bay Bridge connects San Francisco with Oakland, and is one of the longest suspension bridges in the United States.

This is an interesting look at the construction process of the bridge, having constructed the center road of the bridge instead of building from each, or one side, to connect the roads.

New York City

This photo was taken during the Macy’s Thanksgiving Day Parade back in 1934. Mickey, and 6th Avenue, both have extremely different looks than the way we know them today.

The Macy’s Parade is the second oldest Thanksgiving parade in the United States, with the first celebration occurring in 1924. The Mickey Mouse float has been one of the most popular floats throughout the parade’s history.

San Francisco

Here we can see press, and other spectators looking on as riots occurred on Alcatraz Island in 1946. These people were smart to not get too close to the island.

During its heyday, Alcatraz was one of the worst prisons in America, having held many of the countries worst criminals. The prison was open from 1934 until 1963.


This photo was taken prior to a game of the 1935 World Series, played between the Chicago Cubs, and the Detroit Tigers. As you can see, it is utter chaos outside of Wrigley Field in preparation for the big game.

The Tigers ultimately went on to win the series, and the Cubs didn’t win a World Series until they broke their famous billy goat curse in 2016

New York City

This is a view of the New York City skyline from a boat on the Hudson River back in the late 1930’s. This shows the view of the city from the west side.

As you can tell, the skyline was extremely different than it is today, or even the late 20th century, but was still a grand skyline that amazed people from across the world.

San Francisco

This is a photo of the Golden Gate Bridge under construction back in the 1930’s. As you can see, its pretty cool how the construction of the road stems from the middle to the two sides similar to the Bay Bridge.

The Golden Gate Bridge is the second longest suspension bridge in the United States to this day, and connects San Francisco with Marin County, and is recognized as a symbol of the city, and California.


As we saw before on multiple occasions, Chicago seemed like a mess with cable cars running all over the streets filled with pedestrians.

So it was a good idea for the city to build an elevated subway, which is now known as the “L,” and is the second most used subway in the United States, behind New York’s MTA.

San Francisco

Here we can see a vintage photo of the famous San Francisco cable car. San Francisco’s cable car’s are still a popular tourist attraction to this day.

The actual cable car’s today look different, but the car following behind, causing traffic, is still seen in the modern day.

New York City

Pictured here are two aircraft carriers with the New York City skyline in the background. This is before the time of the Intrepid Museum located on the west side, so this was quite a sight to see for New Yorker’s.

The carriers made their way to New York for a post World War II Navy Day address by President Truman following the big win over the axis powers.

New York City

An over 200 foot radio antenna was put atop the Empire State Building in 1950, a time period where the building began to get more popular due to its reputation.

The addition of this antenna allowed television stations to broadcast from the building, bringing in even more renters and profit. This antenna turned the tallest building in the world into the tallest in the world by far.

New York City

This photo was taken in 1951 in the Bronx, back when drive-in movies were extremely popular as can be seen by the packed lot.

Times have changed drastically from not wanting to get out of your car to see a movie, to not even wanting to get out of bed. Who knows what the future has in store for us.

Los Angeles

The TCL Chinese Theater opened on Hollywood Boulevard in Los Angeles in 1927, with this photo having been taken in the late 1950’s.

The idea for the theater was brought to light due to the success of the nearby Egyptian Theater. The theater is home to many movie premieres, and is recognized all around the globe.

New York City

Coney Island is a must go Summer spot in New York City, and as you can see, many New Yorker’s agree based on this photo from the 1950’s.

The beach is completely packed, and you can see the famous parachute ride in the background on the boardwalk. Although it is the most popular, Coney Island is not actually the only beach in New York City.

New York City

This photo, taken in the mid 1950’s is of Times Square. As you can tell, Times Square of the 1950’s has barely any resemblance to one of the largest tourist attractions in the world.

One of the worlds most visited tourist attractions, getting an estimated 50 million visitors a year, Times Square couldn’t have more of a different vibe in this picture.

Los Angeles

Los Angeles has had two major floods in its history, one in 1938, and the other, pictured below, twenty years later in 1958. The flood was caused from torrential rains.

It is hard to imagine one of the biggest cities in the country looking like this, but Los Angeles wasn’t the same as it is today.


The Seattle Space Needle was built for the 1962 World’s Fair, as both an observation tower, and a restaurant.

The Space Needle has become a landmark of Seattle, and remains one of the largest structures west of the Mississippi.

New York City

“The most famous arena in the world” began construction at its 7th Avenue location above Pennsylvania Station in 1964. This is what The Garden looked like mid-way through its construction, which was completed in 1968.

Madison Square Garden was completed a few years before the Knicks went on to win their first, and second championships, which are also their only two. Little do people know that Madison Square Garden was actually located further downtown on 23rd street prior to its current location.

Las Vegas

The Las Vegas strip clearly wasn’t always as flashy as it is today. This photo, taken in 1967, shows Caesars Palace, along with a bunch of other hotel and casinos scattered along the strip.

The current skyline of the Vegas Strip is entirely lit up, with hotels and casinos all along the strip. Even though the modern skyline is gorgeous, it is amazing to look at what sin city looked like when it was just a random desert city with a few hotel, casinos.

New York City

The World’s Fair took place in Queens, New York back in 1964, two years after the World’s Fair in Seattle. This world’s Fair hosted 80 nations at Flushing Meadows-Corona Park in its over 600 acres of space.

This was actually the second World’s Fair the park had hosted, having previously done so in 1939. This is a beautiful view of the fare, although it is missing the real Queens feel with the highway, and subway surrounding it.