Walter Raleigh’s initial North American expedition is led by Phillip Amadas and Arthur Barlowe, who choose the Outer Banks of modern North Carolina as an ideal location from which to raid the Spanish and proceed to make contact with the natives.

They return to England with a report of their find: samples of the local flora and fauna, and two natives: Manteo and Wanchese.

A colonizing expedition composed solely of men, many of them veteran soldiers who had fought to establish English rule in Ireland, is sent to establish Raleigh’s colony in the spring of 1585.

The leader of the settlement effort, Sir Richard Grenville, is assigned to further explore the area, establish the colony, and return to England with news of the venture's success.

Upon arrival at the Outer Banks, the lead ship strikes a shoal and floods, ruining most of the colony's food stores.

After the initial exploration of the mainland coast and native towns here, a silver cup is noticed to be missing; the chief in the last native town visited is burned to death in retaliation.

Despite a lack of food and this rocky start to relations with a potential neighbor, Grenville decides to leave Ralph Lane and approximately seventy-five men to establish the English colony at the north end of Roanoke Island, promising to return in April 1586 with more men and fresh supplies.

Lane explores Albemarle Sound, at this time called the Sea of Rawnocke (Roanoke Sea).

Relations with the neighboring tribe have degraded to such a degree by April 1586 that they attack an expedition led by Lane to explore the Roanoke River.

His response is to attack the natives in their capital, where he kills their weroance, Wingina.

April passes, and there is no sign of Grenville's relief fleet.

Drake, the first European visitor to the colony since Raleigh’s departure, arrives in June on his way back from destroying the Spanish fort of St. Elena and offers to take the bedraggled colonists back to England; they accept.

Grenville and the surplus arrive shortly after Drake's fleet departs.

Finding the colony abandoned, Grenville decides to return to England with the bulk of his force, leaving behind fifteen men to maintain both an English presence and Raleigh's claim to Virginia.

Raleigh dispatches another group of colonists in 1587.

John White, an artist and friend of Raleigh's who had accompanied the previous expeditions to Roanoke, leads ninety-one men, seventeen women, and nine children, tasked with picking up the fifteen men left at Roanoke and settling farther north, in the Chesapeake Bay area.

The Roanoke settlement is reestablished after forty of the colony's men had already been shipped to Roanoke Island to search for the fifteen men stationed there, but of the men left the year before, only the bones of a single man are found.

The one local tribe still friendly towards the English, the Croatans on present-day Hatteras Island, report that the men had been attacked, and the nine survivors had taken their boat and sailed up the coast.

The settlers land on July 22, 1587 on Roanoke Island.

Governor White's daughter delivers the first English child in the Americas: Virginia Dare, born on August 18.

White had reestablished relations with the neighboring Croatans before her birth, and had tried to reestablish relations with the tribes that Ralph Lane had attacked a year previously, but the aggrieved tribes had refused to meet with the new colonists.

George Howe is killed shortly thereafter by natives as he crabs alone in Albemarle Sound.

The colonists, knowing what had happened during Ralph Lane's tenure in the area and fearing for their lives, persuade White to return to England to explain the colony's situation and ask for help.

There are approximately one hundred and seventeen colonists—one hundred and fifteen men and women who had made the trans-Atlantic passage and two newborn babies, including Virginia Dare—when White returns to England, leaving them with a pinnace and several small ships for exploration of the coast or removal of the colony to the mainland.

The events of the Spanish Armada and its aftermath prevent either its founder, Walter Raleigh, or anyone else from returning to the Virginia coast until August 1590, when the relief ship under Governor John White finds the colony deserted with only the word CROATOAN, the name of a nearby island, carved on a doorpost.

Inclement weather and a tight schedule prevent the relief ship from visiting Croatoan (an island whose Amerind inhabitants will later exhibit a high incidence of gray-eyed individuals inexplicably familiar with Bible scriptures).

After the unsuccessful search, White returns to England on October 24, never to know the fate of his wife and child.