Template:On this day/May 16
- 1719 – The French fleet, under Jean Baptiste Le Moyne and his brother Sieur de Bienville, entered Pensacola Bay, fired on Fort San Carlos, and captured Pensacola.
- 1824 – Edmund Kirby Smith was born.
- 1856 – Construction began on the Alabama & Florida Railroad.
- 2006 – Escambia County Commissioners requested validation of funds for the Southwest Escambia Improvement District, which was approved but later halted by a complaint by Dr. Greg Strand.