Captains and pirates of the 1600s sometimes flew red flags to signal no quarter, while others flew black flags to intimidate merchant ships. Image source: Library of Congress.
Buccaneers, explorers, settlers, and navies often clashed in Chesapeake Bay waters during Colonial times
In the 1600s, everyday Europeans may not have known much about the New World, but the sea going “navies” of England, Holland, and Spain were familiar with it, and especially of the Chesapeake Bay. Spain saw the region as a habitat for buccaneers. With its many tributaries, it was well suited to offer protection for ships and the captains dedicated to plundering. The swashbuckling pirates that we envision from centuries ago may have sailed far up and into the Bay, but most skirmishes of piracy were between rival Englishmen exploring the Mid-Atlantic coast.
Kent Island, for example, was settled by William Claiborne, a member of Virginia’s Governor Council, and served as a major trading center for early settlers and Native Americans. As early as the 1620s, Claiborne led 100 Virginians to settle the land of Kent (named for his native English home) and built mills as well as a fort and homes.
Portrait of George Calvert (1580–1632), 1st Baron Baltimore. Vintage etching circa 19th century.
The area, though claimed by Virginia, became instantly controversial with Sir George Calvert (Lord Baltimore) of the Maryland colony declaring he, in fact, had a patent on the area. The King of England refused to settle the controversy and the first naval battle between English men took place near Kent leading to charges of piracy.
Virginia’s Claiborne continued to spar with Maryland’s Calvert over trade, causing some Virginians to vow “they would rather knock their cattle on the head than sell them to Maryland.” Claiborne stood strong on his claim to Island of Kent. Politically, Calvert had a stronger voice with the King of England and eventually Maryland would win the land of Kent.
Claiborne was charged with piracy along the Eastern Shore on behalf of Virginia. He became an outlaw in Maryland and would lose his colony lands and estates. Calvert and Maryland simply had more political force in England. Virginia abandoned Claiborne and ceded the island and others in the Bay to Maryland.
Meanwhile, back in England, its government was experiencing a parliamentary crisis. While Maryland and Virginia were loyal to the King, both colonies would be affected by the home country’s preoccupancy of its own, internal struggles. Without England’s naval support, anarchy and piracy would rule the Chesapeake Bay into the early 1700s. Plundering escalated with more and more Dutch incursions into the Bay and self-styled pirates such as Richard Ingle became more prominent.
Kent Island was one of the most controversial settlements in the 1600s, as both Maryland and Viriginia laid claim to the land, leading to conflict and accusations of piracy.
Ingle was a loyal Protestant driven by revenge and determined to plunder the Papists of Maryland in its capital of Saint Mary’s City. He was joined by Claiborne, who was plotting his own resurgence. Ingle focused on the estate of one of the richest men in Maryland, Captain Thomas Cornwallis, who had previously captured the Island of Kent for the Calvert family. What Ingle and Claiborne found was a lavish estate designed with art and fabrics from around the world and farmlands and animals. The plunders preceded to kill the animals and burn the house down after plundering the household wares and arts.
Ingle then set forth on a reign of terror against Maryland—a colony founded by a Catholic population—forcing many to flee to Virginia, while the Protestants continued to pillage their neighbors.
Shipping was threatened. The Governor of Virginia declared the Bay is “so full of pirates, it is impossible for any ship to go home safely.” Ships were outfitted for war and traveled together in fleets to move the cash crop tobacco back to England. Royal Navy warships sailed out of England to escort ships transporting goods from Maryland, Virginia, and the Chesapeake Bay.
The chaos finally curtailed when Ingle returned to London and with the simultaneous ascendancy of the Lords of Baltimore (six Calverts across several generations would hold the title), who worked tirelessly to return the colony of Maryland back to prosperity and stability.
Map titled Virginia and Maryland by Francis Lamb that appeared in The Theatre of the Empire of Great Britain, 1676. From the Huntingfield Collection, Maryland State Archives.
Eventually, the most valuable commodity of the New World, tobacco, would be eclipsed by other precious resources and trade preferences. A new form of piracy, however, would emerge in the Chesapeake Bay by the 1800s…focusing on the Bay’s prized oyster. New “oyster wars” and piracy were generated until this Bay resource was finally exhausted.
The Chesapeake Bay in the land of pleasant living that we enjoy now, was not a peaceful place during early European settlement. Englishmen waged turmoil against each other for power over trade and land. Religious warfare played a significant role, as did the control of natural resources. Today, we have a serene waterway, a recreational paradise with a few historic telltale signs of this plundering that dogged the area for more than 300 years.
