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| 1585 |
| | | Roanoke Island, off the coast of North Carolina, is settled by the first English colonists in America – with disastrous results | |
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| c. 1585 |
| | | The English artist John White paints the everyday life of the Secotan Indians of America | |
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| 1587 |
| | | A new group of English settlers arrives at Roanoke Island and makes a second attempt at a settlement | |
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| 1587 |
| | | Virginia Dare becomes the first English child to be born in America, on Roanoke Island | |
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| 1590 |
| | | An English ship, the first to arrive at Roanoke Island since 1587, finds no remaining trace of the settlers or their settlement | |
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| 1607 |
| | | Colonists establish the first lasting British settlement in the new world, at Jamestown | |
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| 1608 |
| | | John Smith claims (many years later) that when captured by Indians he was saved from execution by Pocahontas, daughter of the chief | |
|  | Map of Virginia featuring an image of Pocahontas, 1608
National Archives, Kew
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| 1609 |
| | | Henry Hudson reaches the inlet of New York Bay and explores the river now known by his name | |
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| 1613 |
| | | The American Indian princess Pocahontas is taken hostage by Jamestown colonists in the first Anglo-Powhatan war | |
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| 1614 |
| | | Pocahontas is baptized a Christian and marries John Rolfe, one of the Jamestown colonists | |
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