Tales of Piracy on the Chesapeake Bay

Elnicki Wade

There's a bit of pirate in every boater a love of the water, a sense of adventure, and a wink of defiance about following rules. Maybe that's why we're drawn to stories about the swashbucklers who roamed the seas. Movies and folklore tend to focus on pirates of the Caribbean, so most people don't realize that the Chesapeake Bay hosted its share of scallywags and wenches. But why would they choose the waters of Maryland and Virginia when the Atlantic and Caribbean were teaming with treasure-laden ships and ports to plunder?

Several factors made the region a hot-spot for pirates. After months of raiding and pillaging, battle-weary buccaneers ran out of supplies and their ships took a beating. The Bay's isolated necks and coves provided ideal sanctuaries to make repairs and restock stashes of food, water and other necessities.

Plus, pirates also didn't meet much resistance when they cruised into the Bay. In the early 1600s, England and Spain were jockeying for control of the New World, but were often occupied with their own troubles in Europe. Settlers were more concerned about surviving famine, disease and Indian raids.

As the Maryland and Virginia colonies flourished, ships passing through the Bay to and from Europe became filled with treasures that made pirates rub their eye patches in glee. Capturing a merchant ship that carried a cargo of tobacco, food, wine, linens, or gold was cause for wild, and often drunken, celebration.Like a school of piranhas devouring a carcass, pirate crews would strip their prey of sails, rigging and tackle. Sometimes they'd set a crippled vessel ablaze, just to watch it burn. Passengers were forced to join pirate crews or tortured to cough up secrets about royal warships in the area.

If scallywags overtook a ship that was newer or faster than their own, they'd add it to their fleet. This was a huge source of frustration for the Governors of the Colonies, who would convince the king to send battleships to defend their subjects, only to be outgunned and overpowered by invading sea dogs.


Some colonists liked to trade with pirates, exchanging fresh water and provisions for more exotic stolen items such as spices, clothing, or rum. Other colonists became fed up with marauding scoundrels. Take the case of the dreadedMonsieur Peuman, a French privateer infamous for pillaging farms and towns along the Rappahannock River near Port Royal, Va., in the mid-1600s.At wit's end with Peuman's looting, villagers formed a search party to capture the pirate.

When Peuman entered the river, the townsfolk chased his ship upstream. He veered into a creek to evade them but got stuck in shallow water. The angry mob jumped on board, slew the Frenchman, and named the creek Peumansend to mark the place of his demise.


By the late 1600s, England's King James unleashed a brigade of Royal Navy ships to clear out the scoundrels who terrorized the Chesapeake, Caribbean, and Atlantic. In 1684, the King issued a pardon for pirates who turned themselves in to authorities and rejected the pirate way of life.

The previous year, a trio of seasoned privateers named Davis,Wafer, and Hinson had joined Captain John Cook in Accomac, Va., to sail the South Seas. They had attacked and taken towns and ships, crossed the steamy jungles of the Isthmus of Panama on foot, were befriended by savage jungle natives, and wrought unending chaos on the Spanish colonists of Tierre Firme, says Donald Shomette, in Pirates of the Chesapeake. They cruised around the globe, amassing a considerable pirate's bounty along the way.

Captain Cook passed away during the voyage, but the three buccaneers eventually returned to the Chesapeake Bay, hoping to settle down and retire as wealthy men. Near the mouth of the James River, they were apprehended by Captain Rowe of the Dumbarton and tossed in the Jamestown jail. The deal arranged for their freedom required them to hand over their stolen loot, which Virginia authorities used to establish the College of William and Mary.


The Golden Age of Pirates reached a peak from 1690 to 1730. Despite popular perception, Life aboard a sailing ship was anything but comfortable. Seamen lived in cramped and filthy quarters. Rats gnawed through anything, including a ship's hull. Food spoiled or became infested, and fresh water turned foul, says Cindy Vallar, in Pirates and Privateers,The History of Maritime Piracy.

Life expectancy for a Chesapeake privateer was short. Fierce storms sunk scores of ships, and diseases such as  scurvy, dysentery, and smallpox ran rampant among the crew. But the opportunity to make a mint in pirate booty and live a life of adventure proved irresistible for many fortune-hunters on the Bay.

One of the most formidable pirates was Blackbeard (aka Edward Teach). According to legend, he captured 40 ships in his day, and his physical appearance sent fear running down his enemies' spines. Blackbeard towered at 6-foot 5-inches, with a jet-black beard that grew down his chest and was braided with brightly colored ribbons. A bandolier crossing his chest with six pistols was the finishing touch to his horrifying attire. He drank rum spiced with gunpowder.

The Eastern Shore was Blackbeard's favorite haunt for mending damaged ships. He roamed as far north as Pennsylvania, but loved to dodge British ships by hiding in Pagan Creek off the James River or in the remote corners of Lynnhaven Bay.

Blackbeard's pillaging days came to a screeching halt in 1719, when Lt. Robert Maynard fatally shot him in a bloody fight off North Carolina's Outer Banks. Maynard severed Blackbeard's head and mounted it on his ship's bow.

For years, the skull hung from a pole where the Hampton and James Rivers meet to warn other pirates of how Chesapeake authorities dealt with unwanted scoundrels.

Blackbeard's unlikely partner in crime was a wealthy landowner, named Stede Bonnet, nicknamed The Gentleman Pirate. Even though Bonnet had no experience in sailing, Blackbeard took him under wing, and the polar opposites shared many a conquest along the Atlantic Coast.

The notorious William Kidd allegedly worked his way through the Chesapeake Bay, too. Originally commissioned as a British privateer, some reports suggest that he got off track and turned to piracy... In 1700, he was arrested, shipped back to England, and sentenced to death. The rope broke during his execution, but a second attempt at hanging finished the job. For years, his body hung above the Thames River in a cage called a gibbet, to discourage others from choosing life as a buccaneer.

Kidd accumulated a hefty fortune during his time on the seas, and a portion of his booty was recently discovered on Long Island. But according to legend, not all of his treasure has been found, because he buried it in various spots on the Mid-Atlantic.

So, the next time you anchor your boat on a remote neck of the Bay, don't be afraid to dig in the sand and look for hidden treasure beneath your feet.

Susan ElnickiWade is author of Crab Decks & Tiki Bars of the Chesapeake Bay, Maryland and Virginia Editions.

Want to read more about sea rascals who plundered the Bay?

The definitive resource is Pirates on the Chesapeake by Donald G. Shomette (Tidewater Publishers, ISBN: 978-0-87033-607-2). But if you'd like travel the Chesapeake waters with other buccaneers, the following tours and festivals will help you unleash your inner-swashbuckler:

Capt. Jack's Pirate Ship Adventures (Virginia Beach), 757-305-9700

Duckaneer Pirate Ship Tours (Ocean City,Md.), 410-289-3500

Pirate Adventures on the Chesapeake (Annapolis), 410-263-0002

Urban Pirates (Baltimore), 410-327-8378

Pirate & Privateer Crews

Yorktown Pirate Boat Tour, 757-639-1233

Rock Hall Pirates &Wenches Weekend, (annually in August)

Fells Point Privateer Days, (annually in April)

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