History of the Keys - The Shore Islamorada

Henry Flagler

The area has a colorful history. Native Americans were first to discover the riches of the Keys. Artifacts date the earliest habitation to around 2,000 B.C. In the early 1700's, the Seminoles also began to arrive here. And by the mid 1800's, the first settlers appeared.

Farming was once an important industry in the Keys. By the 1880's, Plantation Key had become famous for its pineapples. Other crops included limes, melons, bananas, tomatoes and potatoes.

"Wrecking" (salvaging) also became a thriving industry, feeding off the large number of ships that went down in the reefs surrounding Islamorada. In 1733, an entire Spanish treasure fleet sank here.

In 1905, the industrialist Henry Flagler attempted the impossible — building a railroad from the Florida mainland to Key West, threading its way from isle to isle across miles of open water. His Key West Railroad was one of the engineering wonders of the world. Completed in 1912, it served as the main transportation route through the Keys until it was destroyed in a storm in 1935.

In the 1920s, the State of Florida set out to build a highway to Key West alongside the famous railroad. At first, ferries were used to connect open water sections of this railroad. After 1935, the state bought the railroad bed and converted some of the bridges into roadways. Many of these remain in use today.

Completed in 1938, U.S. 1 is a continuous road from the tip of Florida to Key West, crossing 42 bridges, and offering drivers a breathtaking expanse of water and sky.

Over the years, the Keys have worked their magic on writers and artists. Tennessee Williams and Truman Capote were visitors. Ernest Hemingway, Zane Grey, John Dos Passos and John James Audubon lived and worked here.

The Long Trestle between Long Key and Lower Matecumbe Key, c.1910

Airline Areomarine flying boat, c. 1920

Widening railroad for a highway bridge c. 1936

The first private rod & reel club on the keys, Upper Matecumbe Key, c. 1918

Former President George H.W. Bush with fly fishing expert, Sandy Moret	Jimmy Stewart with bonefish and legendary fishing guide, Jimmy Albright
Fishing great, Carl Navarré with tarpon	Ted Williams with famous fishing guide, Stu Apte

Looking Back