Billy Bowlegs' pirating activities began in the 1830s, when he started attacking American and European ships in the Gulf of Mexico and along the Florida coast. He targeted vessels carrying goods such as cotton, tobacco, and lumber, often using his knowledge of the Florida waters to evade capture.

The reign of pirates in the Gulf of Mexico came to a grinding halt by the 1820s. Following the War of 1812 and the purchase of Florida from Spain in 1821, the United States government made the suppression of piracy a top priority. The U.S. Navy, led by aggressive commanders, began to sweep the Gulf, capturing or killing notorious buccaneers.

The festival features parades, costume contests, a "pirate landing," and a massive treasure hunt for the kids. It is a classic, family-friendly Florida tradition that has kept the name Billy Bowlegs alive for over 70 years.