The settlers eventually turned on the Powhatan Indians. The Jamestown settlers captured the seventeen-year old Pocahontas. During her captivity Pocahontas caught the eye of John Rolfe. John and Pocahontas were married and a permanent peace with the Powhatan Indians was established. John Rolfe, with his Powhatan bride sailed back to London with a Virginia tobacco seed and tobacco became a huge success.

Stephen Hopkins returned to England [maybe with John and Pocahontas] sometime after 1611. Stephen married a second time at St. Mary's Whitechapel in London on 19 February 1618 to Elizabeth Fisher. Elizabeth had a daughter by her first husband. [Did Stephen's first wife die or give-up on her seafaring husband?] Stephen and Elizabeth had a baby, named Damaris, in 1618.

A group of separatists from the Church of England establish a congregation and emigrated to Amsterdam and then moved to Leyden. Although they enjoyed religious freedom in Holland, they found their children losing contact with their English culture. The Leyden group negotiated with the Virginia Co. for the right to settle a colony within their borders in Virginia. The group left the Netherlands for England. When their ship proved unseaworthy, it was abandoned and the entire company crowed aboard the Mayflower.

Stephen Hopkins was not of the Pilgrim company at Leyden, Holland, but embarked with them at Plymouth. The "Mayflower" sailed from Plymouth, England on 16 September, 1620, with 102 passengers. His party aboard the "Mayflower" consisted of his second wife, Elizabeth, her daughter, his two children from Constance (Constance Hopkins and Giles Hopkins), their first born child (Damaris), plus two servants (Edward Doty and Edward Lister).

Stephen Hopkins was one of the twelve Mayflower passengers who had the title of "Mr", which was originally the abbreviation for "Master" and used only by persons of high social rank or learning. While the Mayflower was at sea, Elizabeth gave birth to a child in October or November, which they named "Oceanus".

Rough seas off the coast of Nantucket forced Captain Jones of the Mayflower to alter his course from the mouth of the Hudson River toward Cape Cod, causing conflict between the Pilgrims and those aboard who were not Pilgrims. Fearing further dissention the Pilgrim leaders drafted an agreement, known as the Mayflower Compact, to establish a plan for government. Stephen Hopkin's name was the fourteenth signer of the famous "Compact" drawn up and signed in the cabin of the "Mayflower" on 21 November 1620.

The ship reached the Cape Cod coast in Mass 65 days after it sailed and dropped anchor off Providence Harbor on 21 November 1620. It reached Plymouth on 26 December 1620, after a small party had explored the site and decided to make Plymouth their new home.

Stephen Hopkins was a member of the first expedition, consisting of sixteen men, that left the "Mayflower on 11 December 1620, and went ashore at Plymouth Rock to find a place for landing. In 1621, Stephen was a part of the first embassy sent to conclude a treaty with the Great Sachem (king) Massasoit, at Pokanoket. Their first born, Damaris, died at an early age. It maybe that he died during the first winter, when nearly half the colonists died before a supply ship arrived in the spring of 1621.

Between 1623 and 1626, Stephen Hopkins was a member of the Governor's Council from Plymouth settlement. Between 1632 and 1635 and in 1637, Stephen was a member of the first council of the Governor's Assistants after the incorporation of Plymouth. In 1637 Stephen Hopkins was an Assessor to raise funds for sending aid to Massachusetts Bay and Connecticut colonies in the impending Pequot Indian wars. In 1638, Stephen Hopkins and his two sons - Giles ( 31 years old) and Caleb (15 years old) were among the forty-two who volunteered their services as soldiers to aid Massachusetts and Connecticut.

During this time the Hopkins family grew . . . Elizabeth gave birth to five additional children, all born at Plymouth. Oceanus, who was born on the "Mayflower" died in 1627 at the young age of seven. Constance, who was fifteen when she and her family left England in 1620, will marry Nicholas Snow between 1623 and 1624 at Plymouth.