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Key West History

Key West History

Key West, also known as “Cayo Hueso,” loosely translates into “Bone Key.”

The original inhabitants of the Florida Keys were the Calusa people. The Calusa people inhabited the part of Key West that was above ground and also used this as a grave yard. They also knew that besides Big Pine Key’s “blue hole,” Cayo Hueso was the western most island having fresh water. The first European to visit Key West was Juan Ponce de León in 1521. He noted the island was littered with the remains (bones) of prior native inhabitants. This is how the island became known as “Cayo Hueso” or Bone Key. Graves of some 295 slaves brought here by slave ship from Western Africa have also been discovered in Key West.  The “African Cemetery” dates back to 1861.  After slaves fell ill on the voyage, once reaching Key West, the US Marshal tried to restore them to good health.  In their 85 day stay here, 295 persons perished and were buried in the “African Cemetery” located near the East Martello Towers. A monument has since been erected to serve as tribute to those who had died.

The East Martello Towers were built during the US Civil War as a blockade and for protection. The towers were never finished, and in 1866, the project was abandoned. In 1763, when Great Britain took control of Florida, the community of Spaniards and Native Americans were moved to Havana. Although Florida returned to Spanish control 20 years later, there was no official resettlement of the island. Informally, the island was used by fishermen from Cuba and from the British Bahamas, who were later joined by others from the United States after the latter nation became independence. While claimed by Spain, no nation exercised de facto control over the community there for some time. In 1856, the Spanish established Key West as a  marine salvage and fishing town.

Who owns Key West (“Cayo Hueso”)?

In 1815, Juan Pablo Salas was deeded Key West by the Spanish governor of Cuba.  At that time, Juan Pablo Salas was  an officer of the Royal Spanish Navy Artillery which had been posted in Saint Augustine, Florida.  In 1821, Key West was transferred to the United States. Juan Pablo Salas then sold the island-twice.  He first traded it for a sloop (a sailing vessel) valued at $575 and later sold it in it 1822 to a U.S. businessman, John W. Simonton. Simonton bought the island during a meeting in a Havana café on January 19, 1822 for the equivalent of $2,000 in pesos.

Meanwhile, the sloop trader sold the island to General John Geddes. Geddes, a former governor of South Carolina, tried to secure his rights to the property before Simonton. Simonton had ties to influential friends in Washington and gained clear title to the island. Simonton heard praises of Key West from his friend, John Whitehead, who bragged  of Key West’s strategic location and

deep harbor Whitehead gained great insight into Key West after being shipwreck here in 1819. At that time, because of its location on the Straits of Florida (the area between the Atlantic Ocean and the Gulf of Mexico), the island was dubbed the “Gibraltar of the West.”

Thompson’s Island

On March 25th 1822, Lt. Commander Matthew C. Perry sailed the schooner “Shark” to Key West and planted the U.S. flag, claiming the Keys as property of the United States. Perry renamed Key West “Thompson’s Island” after Secretary of the Navy, Smith Thompson. He also named the harbor “Port Rodgers” in honor John Rodgers, a hero of the War of 1812 and the President of the Navy Supervisors Board.  In 1823, Commodore David Porter of the United States Navy West Indies Anti-Pirate Squadron was tasked to take charge of Key West under Martial Law and bring a stop to all piracy acts taking place, including slave trading ships. Unfortunately, Porter abused his authority under Martial Law and acted as a dictator.

Founding Fathers

John W. Simonton, U.S. businessman who purchased the island in 1822, subdivided the island into plots and sold three undivided quarters of each plot to John Mountain and John Warner (who resold to Pardon C. Greene), John Whitehead, and John Fleming.

John Simonton spent his winter in Key West and summered in Washington. Simonton lobbied hard for the development of the island and to establish a naval base on the island, he died in 1854.

Pardon C. Greene. Key West’s “Greene Street” is named after him. Pardon C. Greene is the only one of the “founding fathers” who made Key West his permanent home. He became a local business man and Established himself as head of P.C. Greene and Company. He also served on the city council and as Mayor of Key West briefly. He died at the age of 57 in 1838.

John Whitehead lived in Key West for eight years. During this time he was a partner at P.C. Greene and Company from 1824 to 1827. Whitehead was a lifelong bachelor, and left Key West in 1832, only to visiti the island once during the Civil War in 1861. He died a year later in 1862— insert photo “Whitehead Street” is named after him.

John W.C. Fleming was active in mercantile business in Mobile, Alabama. Fleming befriended John Simonton in Mobile and this friendship led Fleming to Key West. He only stayed for only a few months, and in 1822, left for Massachusetts, where he married. In 1832, Fleeming returned to Key West intending on developing salt manufacturing on the island. He would die later that year at the age of 51.  “Fleming Street” is named after him.

The names of the four “founding fathers” of modern Key West will be easily identified while driving around the island. The main streets were named after them when the island was first platted, in 1829 by William Adee Whitehead, John Whitehead’s younger brother. Duval Street was named after the first and longest serving governor in the history of Florida who served from 1822 and 1834. William Whitehead became chief editorial writer for the “Enquirer,” a local newspaper, in 1834, which would later become the “Key West Gazette”.  He preserved the copies of his newspaper and later sent copies to the Monroe County Clerk’s office. These copies would later would give us insight into life in Key West from the 1820′s – 1840′s.

The first Catholic Church, St. Mary’s Star-Of-The-Sea, was built in 1852. Later, in 1864, this would become a landmark and staple for the first Catholic school in south Florida  The convent of Mary Immaculate is now known as Mary Immaculate Star of the Sea School. The school started when the five Sisters of Holy Names of Jesus and Mary arrived from Montreal, Canada.


Immigrating from the Bahamas, many residents of Key West have become known as “Conch” (pronounced ‘conks’). They arrived in increasing numbers after 1830. Many of those who immigrated here were sons and daughters of Loyalists who fled to the nearest Crown soil during the American Revolution. In the 20th Century, many residents of Key West started referring to themselves as “Conchs.” A “Salt Water Conch” refers to someone born and raised in Key West.

A “Fresh Water Conch” refers to someone who was not born here but has lived in Key West for seven or more years. The true definition of a conch refers to someone with European ancestry who immigrated from the Bahamas, when a baby was born, placed a conch shell on a pole in front of their home.

Wealth, Commerce, and Heritage

The key industries in Key West in the early 19th century were fishing, turtling, cigar manufacturing, charcoal making, salt production, and salvage. In the 1860′s, wreckage “ship salvaging” made Key West the largest and richest city in Florida, and the wealthiest town per capita in the U.S.  The salvaging of wrecked ship’s yielded large quantities of fine furniture, chandeliers, and riches beyond dreams. Key West residents would have the finest furniture and chandeliers in the world, recovering these goods from ships wrecked on the reefs surrounding the keys.

In the late 19th century, salt and salvage declined as industries; however, Key West bounced back by gaining a thriving cigar-making industry. The Key West cigar business can thank Cuba’s unsuccessful war for independence in the 1860s and 1870s. This war sent Cubans seeking refuge to Key West. We all know who rolls the best cigars in the world! By 1889, Key West was the largest and wealthiest city in Florida.

U.S. Civil War and Late 19th Century: Cannons, Cannons, lots of Cannons

Fort Zachary Taylor was crucial during the Civil War.  Although Florida had joined the Confederate States of America, Fort Zachary Taylor was under the control of the Union. Prior to the war, the Fort had already been established as a Naval base, and it contained the largest collections of cannons ever discovered in one place during the Civil War.  During this time many locals were sympathetic to the South and flew Confederate flags over their homes.

The construction of Fort Zachary took place from 1845 to 1866. Construction also began in 1861 on two other forts, the East and West Martello Towers. The Towers served as side armories and batteries for Fort Zachary. East and West Martello’s were connected to Fort Taylor by railroad -tracks for movement of munitions.

Fort Jefferson was located about 68 miles west of Key West at the Dry Tortugas on Garden Key. Fort Jefferson served as the prison for Dr. Samuel A. Mudd who was convicted of conspiracy for setting the broken leg of John Wilkes Booth, the assassin of President Abraham Lincoln. On February 8, 1869, Mudd was pardoned by President Andrew Johnson. He was released from prison on March 8, 1869 and returned home to Maryland on March 20, 1869.

Today, the Fort is a Historic State Park. Each year, the Civil Wars Days reenacted land and sea battles at Fort Zachary Taylor and provides an opportunity to experience keys life as it was in the 1800’s.

Henry Flagler and the Overseas Railroad

The Overseas Railroad was an extension of the Florida East Coast Railway to Key West, located 128 miles beyond the end of the Florida peninsula and into the Florida Keys eventually to Key West. Work on the railroad started in 1905.  Henry Flagler was an axiom in Rockefeller, Andrews and Flagler and also later in Standard Oil during the Gilded Age in the United States. The ambitious Flagler took interest in Florida while seeking a warmer climate for his then sick first wife in the late 1870s. In 1881, he returned to Florida and became a builder and developer of resorts,  hotels and railroads along the east coast of Florida. Flagler began in St. Augustine and then moved progressively south. Flagler helped develop much of Ormond Beach, Daytona Beach, and Palm Beach, and he became known as the “Father of Miami, Florida.” Flagler’s railroad networks became known as the Florida East Coast Railway (FEC).  When the railroad reached Miami in 1896, Flagler knew how close he could be to Cuba by extended his railroad into The Florida Keys. The outermost key, Key West, was only 90 miles from Havana, Cuba. Key West was also closer to the Panama Canal (then under construction) than any other U.S. port.

In 1904, Flagler decided to extend his railroad to Key West. This would be challenging feat considering he would be facing hurricane and labor issues. The first portion of the line, from Homestead to Key Largo, stretched across a swamp now called the Everglades. Once reaching Key Largo, another problem would present itself-insects. The biggest challenge was neither terrain, nor insects but was instead the weather.  In September 1906, a hurricane destroyed the initial work on the Long Key Viaduct and killed more than 100 workers. In 1907, the opening of Long Key Viaduct, more than two miles of concrete arches allowed service to begin to Knight’s Key.  Knights Key also served as a marine terminal. Hurricanes in back to back years (1909 and 1910) destroyed much of the completed railroad. By now, Flagler was 80 years old and wanted to ride all the way to Key West on his railroad before his death.  With the Seven Mile Bridge portion completed, this assured Flagler, and many, that the railroad would soon be completed. Flagler, arrived in Key West on January 22, 1912. By now he was physically frail. He rode aboard his private railcar “Rambler” and told a welcoming crowd, “Now I can die happy. My dream is fulfilled.”  Regular service on the 156-mile Overseas Railway began the following day.

When completed,  Henry Flagler’s Overseas Railroad was named  “The Eighth Wonder of the World.”  At that time, a traveler could venture from New York to Key West by railroad and then take the “Havana Special,” a steamer and car ferry from Key West to Havana.  Flagler died in May 1913, 18 months after realizing his dream.. The railroad operated from 1912 to 1935, until a devastating hurricane on Labor Day washed away 40 miles of the Middle Keys section of the line.  The railroad was never rebuilt, US 1 now resides on a number of the bridges Flagler built.