The Colonial Settlements Timeline

Most historians agree that one of the most misunderstood chapters of American history is the settlement timeline. The way it is often taught—especially to children—creates a simplified, storybook version of events that leaves out the true scope and complexity of colonial settlements.

This oversimplification starts early. Because history is a subject that demands understanding of multiple factors—geography, politics, economics, and culture—it can be challenging for young minds to grasp. To make it engaging, we break history into bite-sized stories. While that approach works for early education, it can lead to persistent misconceptions later in life.

We’ve all heard some of these myths. The Pilgrims landed at Plymouth and celebrated the first Thanksgiving with turkey. George Washington chopped down a cherry tree. Abraham Lincoln freed the slaves with a single act. These stories are memorable, but they don’t tell the full truth. The same is true when we look at the actual sequence of colonial settlements in the Western Hemisphere.

Many Americans believe the Pilgrims were the first to establish an enduring English presence in North America, sparking the creation of the original thirteen colonies. But in reality, colonial settlements began decades earlier and followed a much broader pattern of expansion—one that stretched far beyond New England.

The First English Attempt: Roanoke

By 1580, England was a small island nation with big ambitions. Eager to compete with Spain and other European powers, England set its sights on the New World. The first attempt came in 1584, when two vessels led by Sir Walter Raleigh arrived at Roanoke, Virginia. Over the next six years, ships traveled back and forth between Roanoke and England. But by 1590, the inhabitants had mysteriously vanished, giving rise to the enduring legend of the “Lost Colony.”

While Roanoke failed, it marked the start of England’s push for overseas colonial settlements.

Turning to the Caribbean: Barbados

Ten years later, England shifted its focus southward. In 1600, they successfully established a settlement on the island of Barbados in the southern Caribbean. This colony thrived quickly, producing sugar and attracting English settlers in large numbers. Over time, England expanded to create more than thirty-four other colonies in the Caribbean region. These colonial settlements proved highly profitable and set the stage for further expansion.

Jamestown and the Middle Colonies

Seven years after Barbados, England turned its attention back to North America. In 1607, the Jamestown settlement in Virginia became the first permanent English colony on the continent. Jamestown is often considered part of the “middle colonies” in the settlement timeline, and predated the famous Pilgrims by thirteen years.

Life in Jamestown was harsh, marked by periods of starvation, conflict with Indigenous peoples, and political challenges. Yet it endured, paving the way for more English colonial settlements in the region.

The Pilgrims and the Northern Colonies

In 1620, a group of religious phonatices and businessmen—now collectively known as Pilgrims—set sail aboard the 106-foot Mayflower. Originally bound for Jamestown, storms blew them off course, and they landed in Cape Cod. Eventually, they chose Plymouth as their permanent home, establishing what historians call the northern colonies.

While popular culture often treats Plymouth as the beginning of the colonial story, it was actually just one chapter in a much larger expansion effort. By the time the Pilgrims arrived, England already had successful colonial settlements in both the Caribbean and Virginia.

The Southern Colonies and Charlestowne

By 1670, the British Empire had grown rapidly, but it faced a challenge—feeding its growing population across its colonies. To address this, England established the settlement of Charlestown (modern-day Charleston, South Carolina). This marked the beginning of the southern colonies, where agriculture—particularly rice, indigo, and later sea island cotton—would dominate the economy.

Expanding North Again: Philadelphia

In 1682, England turned its attention back toward the north. Philadelphia was founded as part of the northern colonies, offering a strategic and economic hub for trade. The city quickly became one of the most important colonial settlements in North America, known for its diversity, commerce, and political influence.

The Final Chapter: Savannah

The settlement timeline concluded in 1733 when James Oglethorpe and nineteen associates established Savannah, Georgia. Savannah was founded as a buffer colony to protect the Carolinas from Spanish Florida, and it became the last of the original thirteen colonies to be established.

The Bigger Picture

From 1584 to 1733, England expanded from a small island nation to a global empire with more than 105 colonial settlements worldwide. The thirteen American colonies, while important, were only a small part of this vast network. Caribbean colonies, in particular, generated immense wealth for Britain and often overshadowed the American settlements in economic significance.

When we compare the actual timeline of colonial settlements to what we were taught as children, the differences are striking. The Pilgrims were not the first English settlers in the New World. Jamestown preceded them by over a decade, and Roanoke was attempted decades before that. Barbados and the Caribbean colonies were already thriving before Plymouth was even founded.

The reality is that England’s colonial settlements developed in a complex, strategic pattern shaped by economic needs, political rivalries, and geographic opportunities. The story of America’s thirteen colonies cannot be understood without seeing it in the broader context of British global expansion.

Understanding the real sequence of events not only corrects historical misconceptions but also gives us a richer appreciation for the challenges and ambitions that drove England to establish its colonial settlements. This wider lens reveals a more accurate and fascinating history—one that goes far beyond the simplified tales we learned as children.