Key West used to look like that? See old photos of Duval Street, attractions and bars

Jeff Kleinman
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Like most places, Key West has changed through the decades.

Tourism became the economy’s bedrock. Chain stores moved downtown. More people, more cars.

But the Southernmost City is still a small town with a sense of history. You may not recognize some places on Duval Street anymore, but the heart of Key West has remained.

MORE PHOTOS: Downtown Miami used to look like that? See old photos of streets, buildings and cars

Take a look at what a few Key West spots looked like in past decades through the archives of the Miami Herald:

RESTAURANTS

Shorty’s Diner on Duval Street was a favorite of President Harry Truman, who walked to breakfast when he stayed at the Little White House in Key West. Shorty’s closed in 1989.
Shorty’s Diner on Duval Street was a favorite of President Harry Truman, who walked to breakfast when he stayed at the Little White House in Key West. Shorty’s closed in 1989.
Blue Heaven in Key West in 1985.
Blue Heaven in Key West in 1985.
Logan’s Lobster House.
Logan’s Lobster House.

CONCH TRAIN

Locals ride alongside the Conch Train in 1981. Tour guide drivers roll up and down city streets and point out landmarks to the tourists on board.
Locals ride alongside the Conch Train in 1981. Tour guide drivers roll up and down city streets and point out landmarks to the tourists on board.
The Conch Train on a Key West street.
The Conch Train on a Key West street.

BAR SCENE

Sloppy Joe’s Bar in Key West in the the late 1930s with the original proprietor, Josie ‘Sloppy Joe’ Russell, center. Russell was immortalized by Nobel Prize winning author, Ernest Hemingway, as the protagonist Harry Morgan in the classic “To Have and Have Not. The original Sloppy Joe’s location is now Captain Tony’s Saloon.
Sloppy Joe’s Bar in Key West in the the late 1930s with the original proprietor, Josie ‘Sloppy Joe’ Russell, center. Russell was immortalized by Nobel Prize winning author, Ernest Hemingway, as the protagonist Harry Morgan in the classic “To Have and Have Not. The original Sloppy Joe’s location is now Captain Tony’s Saloon.
Key West’s oldest bar.
Key West’s oldest bar.
Sloppy Joe’s Bar.
Sloppy Joe’s Bar.

DUVAL STREET

The Strand on Duval Street.
The Strand on Duval Street.
The Kress building on Duval Street in Key West in 1993.
The Kress building on Duval Street in Key West in 1993.
Key West’s Duval Street in 1976.
Key West’s Duval Street in 1976.
The San Carlos Institute a Cuban heritage center built in 1924.
The San Carlos Institute a Cuban heritage center built in 1924.

LANDMARK SIGNS

A helpful tease on the road to Key West.
A helpful tease on the road to Key West.
A Key West street sign at a well-known intersection.
A Key West street sign at a well-known intersection.
A historic library sign.
A historic library sign.

HOTELS

The La Concha Hotel on Duval Street in Key West in 1978.
The La Concha Hotel on Duval Street in Key West in 1978.
Casa Marina.
Casa Marina.