The most significant event during his term in office was King Philip's War, which created great havoc for both the English and Indian populations and changed New England forever.

[5][6][self-published source][7] In 1643 Josiah Winslow was chosen deputy to the general court from Marshfield, and in 1656 he succeeded Myles Standish as the commander of the colony's military forces.

[citation needed] On September 9, 1675, he signed a Declaration of War made by the commissioners against the Indian leader known as King Philip.

King Philip (aka Metacomet) and Governor Winslow had allowed an acrimonious situation to get out of hand and the attack and the violence that followed surprised everyone – English and Indian alike.

[15] King Philip began his relationship with the English with the best interests of all at heart, but greed played a part in his thinking and he eventually was involved in a large scale transfer of native lands to the colonists, helped by a questionable character, Leiden-born Thomas Willet, who wrongly portrayed himself a friend to all parties.

Shiwei Jiang has several Plymouth deeds showing that Moses Simmons and his son Aaron, early settlers of Scituate, bought some lands from Josiah Winslow and Constant Southworth.

Prence and Winslow tried to emulate the relationship that Bradford and Standish had with the Indians in 1622, but, as recorded by Hubbard, fell short of that goal.

When Prence died in 1673 and Winslow became governor, King Philip was very displeased to have to conduct business with a man he immensely disliked.

[16] At the time that Josiah Winslow became governor of Plymouth Colony in 1673, he was seen by the local native peoples as the embodiment of all that was unwelcome about the relationship between the Indians and the colonists.

But Winslow, by now ill with possible tuberculosis and in no condition to fight a war, whether on purpose or not, managed to work against Philip instead of helping him with the support he badly needed to keep his warriors in check.

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.

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.

[15][22] 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 remembrance of her husband, Penelope had Boston silversmith John Coney place a lock of his hair in a mourning ring.