Photo: In Keys Weekly
“The fifth version of the Key West jail in Jackson Square on Whitehead Street was built in 1892 after a fire had reduced much of the island’s commercial center to ashes a few years prior. With 18,000 residents at the time, the city of Key West was the most populous in Florida, and a stately and solid jail and courthouse was designed to symbolize that pride — not to mention provide a more fireproof facility.

An African-American child of slaves, Charles Fletcher Dupont was elected sheriff in 1888 and was helping to oversee the jail. In 1891, he prevented the attempted lynching of two pro-Spain Cubans accused of murdering a pro-independence Cuban.

Such stories are just the tip of the iceberg for the old Key West jail on Whitehead Street, and, fittingly, it is now in phase three of a renovation that will turn it into a museum, hopefully to open for the 2022-23 tourist season.

The project and construction were approved by the Monroe County commission at its April 21 meeting and is being guided by the Key West Art and Historical Society. The plan is to build a museum that recreates a circa-1900 jail experience and tells Monroe County history. Whitehead Street 500 block looking south from Courthouse about 1900. Monroe County Library Collection.”

— Charlotte Twine, Keys Weekly
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Citizens for a Scenic Florida