The first post office in the Florida Keys was established in Key West during the month of February in 1829. The post office was on the corner of Caroline and Front streets. 

Dr. Henry Waterhouse was named its first postmaster. Waterhouse has been described as having a sallow complexion with sunken cheeks and ill-fitting dentures. His false teeth were said to have been carved from the tusk of a hippopotamus. In 1834, Waterhouse would move to Indian Key with his only son. 

The announcement of the opening of a post office on Indian Key. CONTRIBUTED

The island chain’s second post office had been established at Indian Key the year before, on May 21, 1833. 

Silas Fletcher, considered the island’s first white settler, became its first postmaster. Waterhouse would replace Fletcher to become Indian Key’s second postmaster. On Jan. 17, 1835, Waterhouse decided to venture out from Indian Key in a small boat with his son for a night of fishing. A tremendous gale blew through the darkness. In the morning, it was discovered that Waterhouse had not returned. Boats were immediately launched to search for Waterhouse and his son. Their boat was discovered overturned. Waterhouse and his son drowned in the storm.

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