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Governor of Plymouth Colony (1595–1655)
the Mayflower pilgrim
He is the only original Plymouth colonist with an extant portrait painted from life. This, along with portraits of Winslow's son and daughter in law, and various Winslow family artifacts, are in the Pilgrim Hall Museum, in Plymouth, Massachusetts.

Edward Winslow was born on 18th October 1595 and was baptized two days later on the 20th of October at St Peter's Church, Droitwich in Worcestershire, England. He was the eldest son of Edward Winslow Sr. of Droitwich, in Worcestershire, by his wife Magdalene Oliver whom he had married the previous year at St. Bride's Church, Fleet Street, London. Edward Winslow, the father, according to family records, was born October 17, 1560, and was a descendant of the Winslow family of Kempsey, Worcestershire, a line that had existed in the county at least since 1500. The Winslow estate in Kempsey was called Kersweil with a similar name of Careswell later being given to the gentrified Plymouth estate of Governor Josiah Winslow, son of Edward Winslow and Susanna. Author Charles Banks notes that it is highly probable that this Edward, Sr. was the son of Kenelm Winslow of Kempsey. Author Eugene Stratton believes that no one has been able to discern Kenelm Winslow's ancestry with any certainty. Kenelm Winslow, probably a brother of Edward Sr., born in 1551, was called a resident of Worcester, yeoman, in 1605. It is not certain if the family was gentry, but were at least fairly well off. Edward Sr. was an under sheriff and involved in the salt production trade. Edward Winslow had four younger brothers: Gilbert (who accompanied him on the Mayflower in 1620), John, Josiah, and Kenelm, all of whom followed Edward and Gilbert to America over the next decade. Between April 1606 and April 1611, Edward Winslow attended the King's School at Worcester Cathedral, under Henry Bright. Two years later, in August 1613, he became an apprentice contracted for a total of eight years to John Beale, a stationer and citizen of London. After an apparent legal dispute with Beale, however, Winslow's contract was re made with his being apprenticed in October 1615, for eight years. But Winslow apparently did not fulfill his contract with Beale as about two years later, in 1617, he moved to Leiden, Holland to join the Separatist church there.

In 1617 Edward Winslow traveled to Leiden Holland to join the English exile Separatist church and help Elder William Brewster with his underground (illicit) printing activities. Brewster and young Edward Winslow in 1618 were responsible for a religious tract, Perth Assembly, critical of the English king and his church bishops which caused an angry King James to order Brewster's arrest, sending English government agents to Holland to try to find and seize him. The Pilgrims had bad fortune in this, as Elder Brewster was forced to hide, first in Holland, then in England, from the agents just when the Pilgrims needed his leadership in preparation for their departure for America. On April 27, 1618, Winslow married Leiden Elizabeth Barker, he being called a printer from London. Johnson reports that a search of possible English ancestral and baptismal records for Elizabeth does not reveal anything of note. Winslow quite soon became a leading member of the English exiles meeting as the Leiden church group. On June 10, 1620, Winslow was one of four men – the others being William Bradford, Isaac Allerton, and Samuel Fuller, who wrote a letter representing the Leiden congregation to their London agents John Carver and Robert Cushman regarding the terms upon which the Pilgrims would travel to the Americas. The trip preparations became quite taxing on everyone's patience and pocket book due to the various Thomas Weston financial schemes that used up what monies they had and as author Nathaniel Philbrick wrote: " during preparations to sail for America, the Pilgrims demonstrated an extraordinary talent for getting duped."

Winslow and his wife Elizabeth were part of the Leiden Separatist group who had decided to travel far away from England and the repressive regime of King James I to more freely practice their religious beliefs. Merchant Adventurer investment group agent Thomas Weston assisted in this venture by providing the ship Mayflower for the Pilgrim's journey. Traveling on the Mayflower in company with the Winslows were his brother Gilbert and family servant/employee George Soule and a youth, Elias Story. Also in the care of the family was Elinor (Ellen) More, a girl of eight years. In all there were four unaccompanied More children from Shipton, Shropshire in the care of senior Pilgrims on the Mayflower: Elinor, Jasper, Mary and Richard. Elinor perished the winter of 1620 with only one brother Richard More surviving. The Mayflower departed Plymouth, England on September 6/16, 1620. The small, 100 foot ship had 102 passengers and the crew is estimated to be approximately 30 but the exact number is unknown. They lived in extremely cramped conditions. By the second month out, the ship was being buffeted by strong westerly gales, causing the ship's timbers to be badly shaken with caulking failing to keep out sea water, and with passengers, even in their berths, lying wet and ill. This, combined with a lack of proper rations and unsanitary conditions for several months, attributed to what would be fatal for many, especially the majority of women and children. On the way, there were two deaths, a crew member and a passenger, but the worst was yet to come after arriving at their destination when, in the space of several months, almost half the passengers perished in cold, harsh, unfamiliar New England winter. On November 9/19, 1620, after about three months at sea, including a month of delays in England, they spotted land, which was the Cape Cod Hook. After several days of trying to get south to their planned destination of the Colony of Virginia, strong winter seas forced them to return to the shelter of Cape Cod hook, now called Provincetown Harbor, where they anchored on November 11/21. The Mayflower Compact was signed that day.

Winslow made several voyages back to England in the 1620s, serving as ambassador for the Pilgrims and negotiating with the colony's financial backers. In 1624, he brought the first cattle – three cows and a bull – to Plymouth. They came from Devon, England, and their descendants became the American Milking Devon breed, which were much valued because they could be used for milk, beef, and as oxen, and were good foragers (did not require supplemental feed). Winslow had established a friendship with native leader Massasoit, whose people were trading with the colonists. In January 1629 a new patent for land at Kennebec was approved which provided for a fishing and trading post at Pentagoet and a fortified trading post at Cushnoc on the Kennebec which opened the area to Plymouth colonists. At the same time, Isaac Allerton opened his own trading post on the Kenebec and thereby became a rival of Edward Winslow, setting a pattern for the adversarial rivalry between them that would continue from that time on. In 1632, he made an exploratory tour up the Connecticut River for colonization. It is suggested that he landed and selected the settlement which became Windsor. Edward Winslow was an experienced diplomat acting for Plymouth in its relationship with English officials. He later was Plymouth governor for one year terms from 1633–34, 1636–37, and 1644–45. Additionally, in 1643 Winslow was one of the commissioners of the United Colonies of New England, which was a military group uniting the various New England colonies against the natives. Winslow lived for a short time in Clapham, Surrey together with a number of radical Puritan merchants, including James Sherley one of the financiers of the Mayflower. These merchants supported his campaign to send missionaries to the Indians in North America. In 1654, Winslow was commissioner of an English naval mission against the Spanish in the West Indies. They were victorious but Winslow contracted yellow fever and died on May 7, 1655, near Jamaica.

Winslow is reported to have been buried at sea in the Caribbean somewhere between Hispaniola and Jamaica, sometime after May 7, 1655. Winslow Cemetery in Marshfield, Massachusetts has a stone monument to "The Settlers of Green Harbor Marshfield" with the name of Edward Winslow and his wife Susanna and many others. This includes the names of Susanna's sons Resolved and Peregrine White and their wives. Also in Winslow Cemetery is a memorial stone with plaque stating "Edward Winslow, Founder of Marshfield".

Gilbert Morris's House of Winslow series covers the family fortunes of Gilbert Winslow and his descendants to the twenty first century.