A Detailed Chronological Account
The 1584 Reconnaissance Mission
Before committing to a full-scale settlement, Raleigh dispatched a reconnaissance voyage in 1584 led by Philip Amadas and Arthur Barlowe. Their mission was to scout the coast and identify a suitable location. They landed on the Outer Banks of modern-day North Carolina and made contact with the local Algonquian-speaking peoples, specifically the Secotan and Croatan tribes. The initial encounters were overwhelmingly positive. Barlowe wrote glowingly of the land, describing it as a bountiful paradise, and of the native people, whom he called “most gentle, loving and faithful.”
This optimistic report was exactly what Raleigh needed to attract investors. To further this, two Indigenous men, Manteo of the Croatan and Wanchese of the Secotan, voluntarily traveled back to England with the expedition. They became sensations at court, learning English and providing invaluable intelligence about their homeland. Manteo would become a steadfast ally of the English, while Wanchese, after observing English society, grew deeply suspicious of their true intentions.
The 1585 Military Colony: A Failed First Attempt
Buoyed by the initial report, Raleigh organized the first colonial expedition in 1585. This was not a settlement of families, but a military and scientific outpost of about 100 men, mostly soldiers, led by the rigid Sir Richard Grenville and governed by Ralph Lane. They established a fort on the northern end of Roanoke Island. The seeds of failure were sown almost immediately. The expedition’s flagship, the Tiger, ran aground upon arrival, ruining a significant portion of their food supplies.
The colony quickly became dependent on the local tribes for food. While relations were initially cordial, the Englishmen’s constant demands and lack of understanding of local customs created immense strain. The colonists, being soldiers, were not farmers and had arrived too late in the season to plant their own crops. As the winter wore on, the Secotan grew tired of feeding the newcomers. Tensions boiled over when Lane, paranoid about a rumored attack, launched a preemptive strike, burning a village and killing its chief, Wingina. This act of violence shattered any remaining goodwill.
By the spring of 1586, the colony was on the brink of starvation. In a stroke of luck, Sir Francis Drake, sailing home from a raid in the Caribbean, stopped at the Outer Banks. He offered to resupply the colony, but a fierce storm scattered his fleet. Faced with a desperate situation, Lane and his men chose to abandon Roanoke and accept Drake’s offer of passage back to England. They had lasted less than a year.
The 1587 Colony: A New Beginning
Despite the failure, Raleigh was determined to try again. He learned a crucial lesson: a successful colony needed to be self-sufficient and populated by families with a stake in its success. The 1587 expedition was different. It comprised 117 men, women, and children, led by John White, an artist and gentleman who had been part of the 1585 colony. Their destination was not the ill-fated Roanoke Island but a new site deeper in the Chesapeake Bay, which was thought to be a more promising location.
However, upon reaching the Outer Banks, the expedition’s pilot, Simon Fernandes, refused to sail them further, insisting they disembark on Roanoke. Whether this was due to a looming storm, a desire to return to privateering, or simple insubordination is unknown. The colonists were left on the same island the previous expedition had abandoned, their fort in ruins and their relationship with the local tribes poisoned by Ralph Lane’s actions. Extensive archives on American history are maintained by the U.S. National Archives and the Library of Congress. Presidential history is documented at The White House historical section.
Despite the inauspicious start, the colonists tried to make a new life. They rebuilt the settlement and attempted to re-establish friendly relations. On August 18, 1587, a significant event occurred: Eleanor Dare, John White’s daughter, gave birth to a baby girl named Virginia. Virginia Dare holds the distinction of being the first English child born in the Americas, a powerful symbol of the hope for a permanent English presence. But the optimism was short-lived. Soon after, a colonist named George Howe was found dead, shot with arrows, a clear sign that at least one local tribe remained hostile.
John White’s Fateful Return and the Spanish Armada
With dwindling supplies and rising tensions, the colonists decided they needed to send a representative back to England to plead their case for support. They chose their governor, John White. He was deeply reluctant to leave, especially with his daughter and newborn granddaughter, but he eventually agreed, promising to return with help as soon as possible. He set sail in late August 1587.
His timing could not have been worse. When White arrived in England, he found the nation on a war footing. King Philip II of Spain, furious at years of English privateering and support for Dutch rebels, had launched the Spanish Armada, a massive fleet intended to invade and conquer England. All available English ships, including those Raleigh had prepared for a relief voyage, were commandeered for national defense. The epic naval battle of 1588, which resulted in a stunning English victory, saved England but sealed the fate of the Roanoke colonists. The war with Spain dragged on, making any non-military Atlantic crossing nearly impossible. John White was stranded in England, separated from his family by a world war.
1590: The Return to a Vanished Colony
It was not until 1590, three long years after he had left, that John White was finally able to secure passage back to Roanoke, joining a privateering expedition. When his party landed on the island on August 18—his granddaughter’s third birthday—they found a scene of eerie silence. The settlement was gone. The houses had been carefully dismantled, not ransacked or burned. The area was enclosed by a defensive palisade, suggesting the colonists had not been taken by surprise. There were no human remains, no signs of a battle or struggle.
The only clues were two carvings. On a tree, they found the letters “CRO.” On one of the main posts of the palisade, the word “CROATOAN” was carved. This was a potentially hopeful sign. Before he had left, White and the colonists had agreed on a secret token: if they had to move, they would carve their destination into a tree. If they were in distress, they would add a Maltese cross above the carving. There was no cross.
“Croatoan” was the name of a nearby island (modern-day Hatteras Island) and the home of Manteo’s people, who had remained friendly to the English. White’s immediate assumption was that the colonists had peacefully relocated there. He was desperate to investigate, but as they prepared to sail south, a powerful storm hit, damaging their ships and forcing the expedition’s captain to abandon the search and set a course for the Caribbean. John White was forced to sail away, never to return. He would die years later in Ireland, never knowing what happened to his family and the Lost Colony of Roanoke.
