Before there was the success of Jamestown, there was the famous failure at Roanoke.
Dispatched by Sir Walter Raleigh in 1587, a group of 150 colonists attempted to settle Roanoke Island. It was the second attempt after an earlier expedition to the same island by Raleigh failed. The new group of colonists would be led by John White, who was a friend of Raleigh and had been on the first trip to Roanoke.
For the second expedition, rather than sticking with a male-exclusive group as was the case with the first, White brought over entire families, including his daughter, who would bear a child on the expedition. The colonists grew to realize that Roanoke Island could not sustain them over the long term, so White returned to England to bring back supplies, leaving the colonists and his daughter and granddaughter.
As a result of conflict with the Spanish, White would not be able to return to Roanoke for three years. Upon his arrival, he discovered no trace of the people he left behind, with no way to find them. Unable to conduct a full search due to the approaching hurricane season, White was forced back to England, never to return. The Roanoke settlers have never been found, and their fate is still a mystery.