Stephen was back in England by 1617, when he married Elizabeth Fisher, but apparently had every intention of bringing his family back to Virginia. Their first child, Damaris, was born about 1618. In 1620, Stephen Hopkins brought his wife, and children Constance, Giles, and Damaris on the Mayflower (child Elizabeth apparently had died). Stephen was a fairly active member of the Pilgrim group shortly after arrival, perhaps a result of his being one of the few individuals who had been to Virginia previously. He was a part of all the early exploring missions, and was used as an “expert” on Native Americans for the first few contacts. While out exploring, Stephen recognized and identified an Indian deer trap. And when Samoset walked into Plymouth and welcomed the English, he was housed in Stephen Hopkins’ house for the night. Stephen was also sent on several of the ambassadorial missions to meet with the various Indian groups in the region.
Stephen was an assistant to the governor through 1636, and volunteered for the Pequot War of 1637 but was never called to serve. By the late 1630s, however, Stephen began to occasionally run afoul of the Plymouth authorities, as he apparently opened up a shop and served alcohol. In 1636 he got into a fight with John Tisdale and seriously wounded him. In 1637, he was fined for allowing drinking and shuffleboard playing on Sunday. Early the next year he was fined for allowing people to drink excessively in his house: guest William Reynolds was fined, but the others were acquitted. In 1638 he was twice fined for selling beer at twice the actual value, and in 1639 he was fined for selling a looking glass for twice what it would cost if bought in the Bay Colony. Also in 1638, Stephen Hopkins’ maidservant got pregnant from Arthur Peach, who was subsequently executed for murdering an Indian. The Plymouth Court ruled he was financially responsible for her and her child for the next two years (the amount remaining on her term of service). Stephen, in contempt of court, threw Dorothy out of his household and refused to provide for her, so the court committed him to custody. John Holmes stepped in and purchased Dorothy’s remaining two years of service from him: agreeing to support her and child.
Stephen died in 1644, and made out a will, asking to be buried near his wife, and naming his surviving children.