Streets of Key West

In 1829 the four owners of the island of Key West, John Simonton, Pardon Greene, John Whitehead, and John Fleming, signed an agreement for the division of the land of the island. They divided Key West into a grid and each block divided into four quadrants, with each owner getting one of the quadrants… Today Key West is a very easy to get around little city because of this grid.

A lot of the streets were named after their daughters. There is a Caroline, Emma, Rose, Margaret, Elizabeth, Petronia, Amelia, Olivia, Angela, Varela, Pearl, and Alberta Street.

The main drag from Route 1 to downtown Key West is Truman Avenue named after President Harry S. Truman. He visited Key West often during his Presidency and used the Commandant’s Quarters on the Naval Base. It came to be known as the Little White House. President Truman spoke to an assembly of all students at Key West High School in 1962 when I was a senior. I don’t remember a thing he said, but I remember that we were warned within an inch of our lives to behave ourselves.

The Presidential Gate

Accompanying note: “Gate adorned with a wreath following the death of former President Harry S. Truman. President Truman was the first president to stay in the commandant’s quarters making it the Little White House.”  (State Archives of Florida/McDonald)

Kennedy Drive and MacMillan Ave are named for President John F. Kennedy who visited Key West in 1962 with Prime Minister Harold Macmillan of the United Kingdom. They had a fast drive in a convertible from Boca Chica Naval Base to the Presidential Gate. There were twelve cars of notables with them. Many Key Westers lined the streets to wave. I was one of them. It was rather a subdued crowd because they were there to discuss the Cuban Missile Crisis, but exciting to see nonetheless. There is also a Roosevelt Boulevard, but no one quite remembers when or why he was here.

There are many lanes and alleys in Key West. There is: Poor House Lane, Windsor Lane, Cornish Lane, Rose Lane, Donkey Milk Lane, Hibiscus Lane, Telegraph Alley, and others named after the original Settlers who lived on them; there is Tift’s Alley, Stump Lane, Shippens Lane, and Curry Lane.

The main Downtown Street is DuVal Street, named after William P. DuVal, first non-military governor of the newly acquired territory of Florida. President James Monroe appointed him, which is probably why Key West is in Monroe County. I always thought DuVal Street was Duval Street. Maybe it is by now. Easier on tourists and sign painters. The things you can learn on the Internet just by delving into a little piece of History. The Internet is a trove of information. Someday when I have the time, I’m going to go into ancestry.com, but not yet.