The Boy in the Barrel: A Future Pirate's First Ship

"A branch of a tree his mast, a blanket his sail."

by Dale Cox

Editor's note: To provide readers with more information about William Augustus Bowles, the real person behind the pirate treasure stories still heard in eastern Jackson County, Florida, historian and author Dale Cox is writing a series of new articles. The life and adventures of Bowles and his crews will be commemorated on May 1-2 during Pirate & Heritage Days at Three Rivers State Park.

The signing of a declaration of war against Spain at Estiffanulga Bluff in 1800 (please see GOD SAVE MUSKOGEE: Pirate War on the Apalachicola) brought the enigmatic adventurer William Augustus Bowles into direct conflict with that country. But who was Bowles? And how did his story begin?

The future adventurer and pirate was born in Maryland in ca. 1763 and was thirteen when war erupted between Great Britain and its American colonies. "An artless school-boy, perfectly unacquainted with any mode of life beyond what he had learnt at his father's farm," according to the interviewer who wrote his autobiography, Bowles joined a Loyalist regiment and entered the service of King George III. 

The Battle of Monmouth, where Bowles claimed to fight in a
"flank company." From a painting by Emanuel Leutze.
Berkley Library

He claimed to serve in a "flank company" at the Battle of Monmouth, New Jersey, before sailing with his regiment from New York to Jamaica. This is possible as his regiment was part of the British army at that time. From Jamaica, he sailed with his fellow soldiers to Pensacola where he arrived late in 1778. Bowles was selected as a cadet at Pensacola, a position that allowed him to train to become an officer, but he blew his chances after he failed to return to camp from a brief leave in town. He either deserted or was dismissed from the service.

Destitute and only around 15 years old, the young man was, to paraphrase his biographer, too proud to beg and unwilling to work:

A party of the Creek nation were on their return home from Pensacola, whither they had come to receive their annual presents; and young Bowles, delighted with the novelty of situation now opened to him, joined the party, having thrown his regimental coat, in contempt of his oppressors, into the sea. [1]

Pensacola Bay at Floridatown.

The Native Americans were Seminoles from the Perryman towns on the lower Chattahoochee River. The most important of these communities was Tocktoethla, the village of Thomas Perryman which stood in today's Seminole County, Georgia. The other was Tellmochesses, the town of his son, William Perryman. It stood near Parramore Landing in modern Jackson County, Florida.

Bowles was accepted by the Perryman chiefs and their followers. Both Thomas and William spoke English, as did many of their followers, so it was easy for the young man to talk with them. Thomas Perryman, in particular, liked Bowles. The teenager was restless, though, and remained with his new friends only a few months before he decided to return to Pensacola:

William Augustus Bowles.

When he arrived on the opposite shore of the bay, he found a hogshead [i.e. barrel], which some British ships had left behind them; and Bowles, impatient of delay, without waiting for any other conveyance, like an Eskimaux [i.e. Eskimo], with the difference of a hogshead for a boat, the branch of a tree his mast, a blanket his sail, and a few stones his ballast, navigated the extensive shores of the harbour, in the day procuring the food of life, and beguiling the tediousness of time by fowling and fishing, and at night regaling on his prey; the sky his canopy, and the earth his bed. [2]

The sight of the future pirate bobbing around Pensacola Bay in a barrel with a blanket for a sail must have been entirely novel. His return to Pensacola likely was via the Pensacola-St. Augustine Road, a horse path that connected the capitals of the colonies of East and West Florida. Branch trails from it led to the Perryman towns, while its western terminus was at today's Floridatown in Santa Rosa County.

Bowles continued his adventures around the bay into the winter of 1779-1780, a time during which his biographer admitted that the young man first developed his dreams of glory.

Note: Learn more about the life of William Augustus Bowles in future articles and mark your calendar now to attend Pirate and Heritage Days at Three Rivers State Park in Sneads, Florida, on May 1-2, 2020. Please click here for more information.