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Once in New England, the small Easton family settled first in Ipswich, and then later in Newbury, both in the Massachusetts Bay Colony. While in Newbury, Easton's father became an adherent of the dissident ministers John Wheelwright and Anne Hutchinson. On 20 November 1637, the elder Easton was one of three Newbury men disarmed for his support of these ministers, and the following March he had license to depart the colony. He then went to Winnecunnet, later Hampton, New Hampshire, but was ousted from there as well, and by the end of 1638 he was at Portsmouth on Aquidneck Island in the Narragansett Bay with other followers of Anne Hutchinson.