In 1627 the Governor of Virginia authorized William Clayborne, "Secretarie of State of this Kingdom" to explore and locate the source of the Chesapeake Bay.

During this expedition, William Clayborne chose an island of the Chesapeake, seperated from the main land by what is now Kent Narrows, to establish a trading post. This island is present day Kent Island and was the first settlement in Maryland. The island was already inhabited by the Matapeakes, a branch tribe of the Ozinies who lived on the southern banks of the Chester River, and the Monoponsons who lived on the southern part of the island.

The early settlers were subject to fatal attacks by the Wicomese from the mainland Eastern Shore and the Susquehannas from the north. In 1641 the indians became so hostile and troublesome the law forbid the settlers to shoot, wound or kill any any indian coming onto the island and forbid the colonists to be friendly. It wasn't until the 1750's that the last indian left the island to settle elsewhere.

The early settlers also found the island to have plenty of wolves, bears, deer, raccoons, foxes, opossums, squirrels, rabbits, beaver and muskrats to hunt for fur.

By 1631 William Clayborne and Rev. Richard Jones had established a settlement on the island. William Clayborne was appointed Commander of the settlers of the Isle of Kent which he named for his home, the County of Kent. Rev. Richard Jones, of the Church of England, aided Clayborne in establishing this Protestant Colony and was the first to preach the gospel in Maryland. Capt. Nicholas Martin represented the Isle of Kent at the Legislative Assembly of Virginia several years before St.Mary's settlement. It wasn't until 1634 that that settlers landed on St.Clement's island.

In 1632, King Charles granted Cecilius Calvert the Charter for Maryland, making the already established settlement on "Isle of Kent" the first in Maryland. It was these adventurers, traders, settlers and their descendants, along with the colonists to follow, that would settle the counties of Kent, Queen Anne's, Talbot, Caroline and Dorchester.