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The History of Old Town Key West

key west aerial view

With its unique location 150 miles south of mainland Florida and at the end of the Florida Keys, Key West has a fascinating history that dates back to the Age of Exploration. Old Town is the most historical part of the island and it’s also where most of the island’s attractions are found today.

Bone Island is Discovered

Ponce de Leon first discovered Key West in 1521 during his expedition to Florida in search of the Fountain of Youth. He named the island Cayo Hueso, which means Bone Island in Spanish, for the bleached limestone rock formation of the island. It was only later that it became known as “Key West,” which sounded like Cayo Hueso to the English-speaking settlers that later appropriated the Spanish territory.

Key West Becomes Part of the United States

The Florida Keys and Key West officially become part of the United States on March 5, 1822 after Lt. Commander Mathew C. Perry sailed the schooner Shark to the island and planted the US flag in the ground. Old Town’s main thoroughfare, Duval Street, was named after Florida’s first territorial governor, William Pope Duval, who held office from 1822-1834. Three notable leaders, James Monroe, John Quincy Adams and Andrew Jackson, appointed him.

Popular Industries

Thanks to the shallow reefs just offshore Old Town and the expansive territory of the Atlantic Ocean and Gulf of Mexico, industries like wrecking, salvaging, salt manufacturing and turtling made Key West the richest city in the United States per capita during the mid-1800s. In 1847, the Key West Lighthouse was built on Whitehead Street to mark the island’s shoreline. Today, you can still scale to the top for a bird’s-eye-view of the island and visit the lighthouse keeper’s quarters.

Civil War & Cuba’s Ten Years War

Leading up to the Civil War from 1845-1866, Fort Zachary Taylor was constructed as a Naval fort at the southern edge of Old Town Key West. While the State of Florida joined the Confederacy, Key West remained a Union territory because of the island’s strong Naval presence.

Key West’s link to Cuba was also established during this time as Cuban refugees of the Ten Years War took shelter in Old Town Key West. A number of historic Cuban-owned businesses and landmarks exist today, including Kino Sandals and the San Carlos Institute on Duval Street. Pepe’s, the island’s oldest restaurant, was opened in 1909 and today is a great spot for a hearty breakfast or grouper sandwich at lunchtime on the shady patio.

Industrial Revolution & Tourism in Key West

With peace restored to the Union, the Industrial Revolution took hold of Key West, starting with Henry Flagler’s Overseas Railway in 1912 connecting Key West to mainland Florida on 128 miles of track. In addition, Pan American Airlines was later founded in Old Town Key West in 1926 providing air service to Havana.

With the island easier to access than ever before, it opened up many outlets for tourism. Notable writers, musicians and dignitaries were also attracted to Old Town Key West. In 1928, Ernest Hemingway and his second wife Pauline first visited. They spent most of the 1930s in a home on Whitehead Street that you can still visit today. Playwright Tennessee Williams became a regular visitor starting in 1941 and is where he wrote the first draft of "A Streetcar Named Desire." He also spent his mornings swimming in the ocean at the end of Duval Street. President Harry S. Truman began making regular visits to Old Town Key West in 1946 during his presidency, eventually transforming the Naval station’s command headquarters into an official Little White House. Today, the Truman Little White House is a museum and event space.

Jimmy Buffett, Fantasy Fest & the Conch Republic

Throughout the 1970s and 1980s, Key West came into its own as an offbeat destination for dreamers who wanted to live by their own rules. Jimmy Buffett arrived in 1971 and the island has been associated with his famous song Margaritaville ever since. Today, visitors can dine at his eponymous restaurant on Duval Street. In 1979, Key West experienced its first Fantasy Fest. The 10-day bacchanal at the end of October is now a legendary annual tradition.

In 1982, when United States Border Patrol officials put up roadblocks at the entrance to the Overseas Highway in an attempt to deter drug smuggling, it resulted in major traffic congestion into the island. The City of Key West responded by briefly declaring its independence from the United States and calling itself the Conch Republic for the first time. This nickname has stuck and Conch Republic Independence celebrations are still held every April. A couple of years later in 1984, Key West’s cruise ship port opened in Mallory Square, allowing another point of entry for tourism to the island.

Treasure hunter Mel Fisher dredged up a piece of Key West’s history from the bottom of the ocean floor in 1985 when he discovered the 1622 wreck of the Spanish galleon Atocha. From “pieces of eight” gold coins to Fisher’s exciting life, you can learn all about his discoveries today at the Mel Fisher Museum.

A Tour Through History

Key West is a thriving island city with a strong connection between history and culture. This is apparent in the Victorian and Colonial architecture of conch cottages and mansions preserved throughout Old Town, as well as many long-standing, locally-owned restaurants, bars and businesses. You can visit the Custom House Museum to view fascinating primary documents and artwork depicting Key West through the ages or go for a spin on the Conch Tour Train to see it all unfold before your eyes.