Josiah Winslow married Penelope Pelham by 1651 and had four children. Children of Josiah and Penelope Winslow, all born in Marshfield, Plymouth Colony: • (infant), born and died March 1658. • Elizabeth, born April 1664 and died June 11, 1735. She married, September 4, 1684, Stephen Burton as his 2nd wife. They had three children. • Edward, born and died May 1667. •
Isaac, born 1670 and died December 6, 1738. He married, July 21, 1700, Sarah Wensley (or Hensley). She died December 16, 1753. They had two children. He was buried in Winslow Cemetery, Marshfield, Massachusetts.
Isaac Winslow had an exemplary career in colonial military and governmental affairs. The
Isaac Winslow House was built on the original homestead of Gov.
Edward Winslow (Isaac's grandfather) and still stands in Marshfield. was built by Josiah Winslow's son. This was the third house built on land granted to Josiah's father, Edward Winslow, in the 1630s who erected the first homestead there. Josiah Winslow married Penelope Pelham in England in 1651, she being born about 1633. Her parents were Herbert Pelham, Esq., and Jemima (Waldegrave). Both parents had extensive noble lineage from England and elsewhere in Europe. Herbert Pelham, as well as his father-in-law Thomas Waldegrave were members of the "Adventurers" which provided investment in the
Massachusetts Bay Company (later Colony) at its beginnings in 1630. Pelham advocated new settlement in
New England and came to that colony with his family in 1638, being involved with the new
Harvard College at
Cambridge. At that time he was a young widower, his wife Jemima having just died, leaving him with four children including 5 year-old Penelope. Pelham soon married a young widow, Elizabeth Harlakenden. In 1643 Herbert Pelham was appointed treasurer of Harvard and in 1645 became Assistant to
Governor Thomas Dudley. In late 1646 the Pelham family returned to England, where he had retained extensive family properties in England and Ireland. On the same ship going to England, they encountered Edward Winslow, who a few years later would be Penelope's father-in-law. Winslow and Pelham had known each other, Pelham having witnessed a letter Winslow wrote to colony Governor Winthrop in 1644, and several years later worked together in England on colony-related business. In England Penelope may have learned about the life of an upper-class gentlewoman from her stepmother. In 1651 Josiah Winslow traveled to England to see his father who, in 1646, had joined the Puritan Protectorate government of
Oliver Cromwell. Sometime between 1646 and 1651 Josiah met Penelope in England and it is believed they were married in 1651, which is when they, and Edward Winslow, all had portraits painted, seemingly as companion pictures. These paintings hang today in the
Pilgrim Hall Museum. Josiah and Penelope returned to Plymouth from England in 1655, the same year his father died at sea as part of a Caribbean naval expedition. In the 1660s the Winslows took up residence at the family estate of Carswell in Marshfield, which was named for the English estate of Josiah's great-grandfather. Josiah enjoyed the distinction of being accomplished in the manner of an English gentleman, married to a quite wealthy and beautiful English wife. == Death and burial of Josiah and Penelope Winslow ==