Welcome to Kent Island, the largest island in the Chesapeake Bay, the Gateway to Maryland’s Eastern Shore, aka the Land of Pleasant Living, and our country’s third oldest permanent English settlement, predated only by Jamestown, Virginia and Plymouth, Massachusetts.

Kent Island’s founder, William Claiborne was born in England around 1600. The son of a merchant, Claiborne was, as a young man, intrigued by Captain John Smith’s explorations in the New World’s Chesapeake region. When he was twenty years old, fashionable, handsome, and good with a sword if somewhat short in stature,  Claiborne sailed to Jamestown to work as a surveyor. With his loyalty to the establishment, proven mettle, and skillful performance of his duties, Claiborne quickly rose through the ranks of Jamestown’s leadership. In 1626 he served as the colony’s Secretary of State and in 1627 was granted a license to trade with the native tribes of the upper Chesapeake.

William Claiborne 2

George Calvert was a privileged gentleman, a close confidante of King James I, but Catholic in a Protestant ruled country hostile to  the Church of Rome. With the king’s royal patronage and protection, Calvert was allowed to leave England and was granted a lordship in Ireland where he was appointed Baron Baltimore of  County Longford.


George Calvert dreamed of a sanctuary for religious freedom, where believers of all creeds could intermingle and create a society made stronger by the diversity of faith.

In 1620 Lord Baltimore was allowed to buy a tract of property in Newfoundland to establish his progressive minded colony, but found the terrain and weather so brutal, he was forced to eventually abandon the venture.


Baltimore visits Jamestown in 1629 and sails quickly back to petition from the king a land grant on the Chesapeake Bay for everything north and east of Potomac River.

Which includes what would become Kent Island.

Which the Virginians considers to be theirs.

In August, 1631, feeling the encroaching threat of the Calverts, the colony of Virginia sends their man Claiborne up the bay to establish a trading post, to plant a flag so to speak. Certain to have noted the real estate while on earlier explorations –  not only is it the largest in the Chesapeake, but is also centrally located and offers excellent bayfront for shipping,  as well as all kinds of nooks and crannies, creeks and coves which could provide protection not only from the elements, but from potential attackers –  Claiborne purchases the island from the natives for about 12 pounds sterling and names it the Isle of Kent to honor his home province back in England.

Scan0001Courtesy: Trudy Guthrie

By that October, Claiborne has built a small fort, with one big home and several smaller ones, and was soon operating a fledgling shipyard, all powered by two large windmills. He  also helps establish the Episcopalian Christ Church Parish, today the oldest active congregation in the state of Maryland.

George Calvert dies before his grant is approved. His son, Cecilius, the 2nd Lord Baltimore, and Cecilius’ brother Leonard, start planning for their Maryland colony, the fulfillment of their father’s dreams of a haven for religious liberty. In March, 1632, Leonard and about 140 traveling companions sail up the bay on the large ship ARK, escorted by the smaller, but armed, vessel DOVE, and set up camp just north of the Potomac, founding what they call St. Mary’s City.

Claiborne is notified his trading license is no longer valid in Maryland.

Tensions mount.

Accusations fly back and forth.

Local tribes are lied to and used for propaganda purposes.

In April, 1635, Claiborne sends Captain Thomas Smith out on the small ship Long Tayle – claimed to be the first English style ship built with indigenous Chesapeake Bay wood – to do some trading. Smith’s crew encounter Henry Fleet, Claiborne’s business rival and a confidante of Calverts. There’s a skirmish – the Long Tayle is confiscated, and two weeks later there’s another altercation, but this time there are four deaths, three of them Claiborne’s men. The surviving Kent Islanders barely make it home alive and are condemned by Maryland as pirates, the first such charge noted in the American colonies.

Virginia is feeling political heat over the Kent Island situation, and they have other, bigger problems to contend with. Their support for Claiborne’s efforts to hold the island weakens.

Cloberry & Company, the financiers of Claiborne’s venture, call him back to England. They send a young man named George Evelin to review Claiborne’s books and manage operations on Kent Island in the founder’s absence. At first, Claiborne believes Evelin friendly, but as soon as Claiborne leaves town, the new management cozies up to the Calverts and helps shut Claiborne out.

In 1638, while Claiborne is in England defending himself to the king and his financial backers, Maryland forces land on the island and take over Claiborne’s fort and home. They round up dissidents and confiscate property. Resisters are accused of various crimes, but offered pardons if they swear an oath of allegiance to Lord Baltimore and the Maryland colony. Captain Thomas Smith, loyal to Claiborne to the end, is hanged after twice being charged with inciting rebellion.


After years of attempts, legal and otherwise,  to retake what he saw as his, Claiborne eventually moves back to his 5,000 acre estate Romancoke on the Eastern Shore of Virginia, where he dies in 1677.

But as long as he does live, William Claiborne challenges the legitimacy of Maryland’s claim to Kent Island, harbors bitter resentments, and ceaselessly bad mouths his enemies.

Which sets a real precedent here on the Chesapeake Bay’s stubborn-in-nature Eastern Shore.

Because if there’s one thing we know how to do, it’s how to hold a grudge.



10 thoughts on “BACK TO THE BEGINNING

  1. Great – can the Heritage Society print in the June newsletter, with your permission, credits, artwork? Martha

  2. Brent I love what you write. So easy to read and informational. I love stuff like this. You are never too old to lean. As they say a mind is a terrible thing to waste…..You truly have a gift for writing…..Keep up the good work…..

  3. Brent I love what you write. So easy to read and informational. I love stuff like this. You are never too old to lean. As they say a mind is a terrible thing to waste…..You truly have a gift for writing…..Keep up the good work…..

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