[11] In early 1609, Stephen Hopkins began employment as a minister's clerk, reading religious works to a congregation including members of the Virginia Company.

On 2 June 1609, Hopkins left his wife and family, and in his ministerial clerk's position, departed for Jamestown in Virginia on the 300-ton Sea Venture, flagship of a flotilla led by Sir George Somers.

The Sea Venture was carrying the new Jamestown governor, Sir Thomas Gates, to his post, as well as resupplying the colony with goods and new settlers.

This Hopkins urged secretly, and Gates considered it mutinous, as he insisted on proceeding, and had organized the settlers as a prison labour camp to prevent escapes.

[8]: 162–163 The English in Jamestown, and those later in Plymouth Colony, were the antithesis of each other—with those in Virginia composed of titled leaders who were in charge of often inexperienced settlers as well as soldiers who were veterans of European wars, such as Capt.

What they found there was that the colonists in Jamestown were starving to death due to their inability and in some cases unwillingness to produce food.

Much of this had to do with some settlers feeling it was beneath their dignity to work and the violent abuse they gave the native people, which caused much enmity towards the English.

At his arrival from Bermuda, Governor Gates estimated there was only days worth of food left, and decided to voyage to Newfoundland and from there find a ship heading for England.

[8]: 164  Just as they were preparing to depart, an English ship came into the harbor with supplies and new settlers, along with a new governor, Lord de la Warr.

By 1614, a letter arrived for a "Hopkins" in Jamestown, and it is presumed that this is how he learned of her death, as he did return to England soon afterward to care for his children.

This, combined with a lack of proper rations and unsanitary conditions for several months, is attributed as what would be fatal for many, especially the majority of women and children.

After several days of trying to sail south to their planned destination of the Colony of Virginia, strong winter seas forced them to return to the harbor at Cape Cod Hook, where they anchored on 11/21 November.

Hopkins was a member of the early Mayflower exploratory parties while the ship was anchored in the Cape Cod area.

He was well versed in the hunting techniques and general lifestyle of the Native Americans from his years in Jamestown, which was later found to be quite useful to the Pilgrim leadership.

Over the years Hopkins's assistance to Pilgrim leaders such as Myles Standish and Edward Winslow regarding his knowledge of the local languages was found to be quite useful.

In addition, the Court had several charges against him "for selling wine, beere, strong waters, and nutmeggs at excessiue rates, is fyned.

The inventory was taken on 17 July 1644, and mentions his deceased wife; his sons Giles and Caleb; his daughters Constance, Deborah, Damaris, Ruth and Elizabeth.