#84 The Pirate Billy Bowlegs in Jackson County (100 Great Things about Jackson County, Florida)

William Augustus Bowles

The pirate Billy Bowlegs is #84 on my list of 100 Great Things about Jackson County, Florida.

Please click here to see the entire list as it is unveiled.

Jackson County, of course, is inland from the Gulf of Mexico, yet it has the strongest connection of any place in Florida to the infamous pirate and adventurer William Augustus Bowles. He is the man celebrated in Fort Walton Beach today as the pirate Billy Bowlegs and is often confused with the Seminole chiefs of the same name.

How Bowles came to be called "Billy Bowlegs" is a mystery to me as there is no evidence he ever used the name during his lifetime. That point aside, however, he most definitely was a pirate.

Born in Maryland, he first came to what is now Jackson County during the American Revolution after he was thrown out of the British military. East and West Florida, divided by the Apalachicola and Chattahoochee Rivers, were then colonies of Great Britain. Spain's more than 250 year rule had ended in 1763 when it lost control of Florida in the treaty that ended the Seven Years' War (known in America as the French & Indian War).

Parramore Landing Park

Making his way east from Pensacola, Bowles likely was trying to walk home to Maryland when he became hopelessly lost in the vast wilderness of the Florida Panhandle. Rescued by Creek Indian warriors from the Perryman towns, he was brought to the Chattahoochee River.

The Perryman towns stood on opposite sides of the river near present-day Parramore Landing Park. Thomas Perryman, the half-Creek son of trader Theophilus Perryman, lived on the Georgia side of the river at what later became Fairchild State Park. His son, William, lived in what later became Jackson County at Tellmochesses, a Creek Indian town that stood on high ground back from the river just north of Parramore Landing.

Creek Indian village in Jackson County, Florida

Bowles became closely associated with both Thomas and William Perryman, both of whom had taken up arms along with their people on the side of the British in the American Revolution. By the time the future pirate reached their villages, they had fought against American Patriots in Georgia.

Bowles married into the Perryman family, becoming a son-in-law of Thomas Perryman and brother-in-law of William Perryman. He frequented their towns and was a regular fixture in the Creek Indian villages along the Chattahoochee and Apalachicola Rivers.

Flag flown by Bowles' pirate ships

In the years that followed, Bowles declared himself the "Director General" of the "State of Muskogee." In this capacity, he declared war on Spain and commissioned the "Muskogee Navy," really a flotilla of well-armed pirate ships that attacked merchant shipping in the Gulf of Mexico.

The Spanish Coast Guard sent armed ships to destroy Bowles and his nest of pirates, but the "Muskogee Navy" was too strong for them and proved victorious in a pitched battle at Apalachicola Bay. The Spanish retreated and the pirates continued their depredations.

Uniquely, the crews of the pirate vessels commissioned by William Augustus Bowles included not only white and African American sailors, but Creek and Seminole Indian sailors as well. While his "State of Muskogee" existed only on paper and in his mind, his ships sailed with diverse crews.

Bowles eventually was taken prisoner and died at El Morro Castle in Cuba. What became of his ships - except for one seized by the English in the Bahamas - is not known. His legend lives on at the Billy Bowlegs Festival in Fort Walton Beach and may soon be celebrated in a Pirate Festival being considered for Parramore Landing Park!

The little known fact that the Pirate "Billy Bowlegs" once lived in Jackson County is #84 on our list of 100 Great Things about Jackson County, Florida.

If you missed the earlier post about Bowles' lost pirate treasure, please visit Lost Treasure of the Money Pond.