On 25 April 1629 he and his first cousin Elizabeth Fones were married, to the dismay of the families. The next year, shortly after his father had sailed for Massachusetts, Henry shipped out on the "Talbot" and arrived at the Massachusetts Bay Colony on July 1, 1630. On the very next day, out on an expedition, he drowned while attempting to swim across the river to retrieve a native canoe. He died before his father was aware that he had arrived in America.
His wife Elizabeth and infant daughter, Martha Johanna Winthrop, came to the Colony the following year. By disagreeing with some of the rigidness of life in Salem, and through her several marriages (including one without proof of divorce from the previous husband), Elizabeth would gain notoriety in the colonies, as outlined in the best-selling novel "The Winthrop Woman" by Anya Seton.
According to WARGS, Elizabeth went on to marry (by the end of Jan. 1632) Lt. Robert Feake (1610-1662) and produce a daughter Elizabeth Feake (1633) (ancestor number 1583 of John Kerry); divorced by 1648, she married William Hallett (1616) before 16 July 1649 and produced William Hallett (c1647-1728), who died at Hallett's Cove, NY (Kerry ancestor 786), and Samuel Hallett (c1651-1724) (Kerry ancestor 794). So her grandparents Adam Winthrop and Anne Browne have four lines of descent to Senator Kerry, three through her and down through his mother's father, James Grant Forbes, and one through her Uncle John the first Governor and through Kerry's mother's mother, Margaret Tyndal Winthrop (1880-1970).