In April, 1585, a group of seven ships left England, once again heading to the North Carolina coast.  This group was boosted by the tales of riches from the 1584 trip.  The group of ships was led by Sir Richard Grenville in the ship Tiger.  Simon Fernando was the captain.  John White, a little know artist who is barely mentioned, was also aboard.  After stopping in Puerto Rico for a time, the group reached the Outer Banks of North Carolina on June 26.

As Fernando guided the Tiger into the narrow inlet, the ship struck land and began taking on water.  After attempting to repair the ship, a group of fifty men
led by Grenville set sail in the sounds of North Carolina to explore the area.  These men traveled south to the Neuse River and Lake Matamuskeet, as far west and the Chowan and Roanoke Rivers.   John White was in this group of  men.  He documented their voyages by painting pictures of the natives and their villages as well as the plants and animals of the area.  It is through his eyes that we are able to catch glimpses of life in North Carolina prior to English settlement. 

It was also during this exploration that Grenville and his men had a mishap with a band of Indians.  Grenville demanded the return of a silver cup supposedly stolen from them by a member of one of the tribes.  The cup was not returned.  To show how the natives that the English would not tolerate such acts, Grenville set the village of Aquascogoc on fire. 

Near the end of July, the group landed on Roanoke Island, the site of  their new colony.  In September, 1585, the group was divided.  Part of the group left for England while Ralph Land and 106 men stayed behind to establish a colony. 

The group left on Roanoke Island came to learn a great deal about how the natives hunted, farmed, and fished.  They studied their customs and religious practices.  They also attempted to learn of the riches of the land like gold and silver.  The English were told of great tribes to the east along the Chowan River and of the wealth of the tribes along the Chesapeake Bay. 

Again, this group set sail to explore the lands around them with Manteo as their guide.  They explored areas around the Pasquotank, Perquimans, and Chowan Rivers.  It was along the Chowan River that they met the kind of the Chawanoac tribe, Menatonon.  Menatonon was paralyzed.  The English took advantage of this by taking him prisoner.  He was to take them to the rich lands along the Chesapeake Bay.    Due to lack of food and fear for their safety, this party turned back for home before reaching their destination. 

As more tension grew between the English and the natives, a final severing blow fell when Wingina, a native king was killed by Lane and his men.  Wingina was plotting to destroy the white men who had come to take their land.  He was rousing several of the neighboring tribes who had also come in contact with the destructive force of this English colonists.  Lane launched a surprise attack that had killed Wingina and the trust that had been created.

In June of 1586, Sir Frances Drake arrived along the Outer Banks to check on the colony.  The men were weak and tired.  All but 18 men joined Drake's fleet and sailed back to England.  In haste, three men who could not be located were left on the island.  About two weeks after Drake's group left, Sir Richard Grenville arrived with supplies for the colony.   He found the colony abandoned.  To hold English position, Grenville left 15 men on Roanoke Island.