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Generations of the Winslow Family

Governor Edward Winslow 1595-1655

Edward Winslow grew up in Worcestershire, England and was educated at King's School at Worcestershire Cathedral.  At the age of 18 he was apprenticed to printer John Beal of London.  He soon became acquainted with another printer, Thomas Brewer, and through him became associated with the Puritan/Separatist group of Saint Bride's Church on Fleet Street in London.

In 1617, Winslow jointed the exiled Separatists in Leyden, Holland as a printer and writer.  During the three years he spent in Holland, Edward was involved in the writing and printing of some twenty books supporting the Separatist cause.  The Separatist press at Leyden was seized by English authorities in 1619.

Determined to worship according to their beliefs, the Separatists set sail for America on The Mayflower September 16, 1620.  Edward Winslow was among the 102 passengers, arriving on the shores of New England November 21, 1620.  After losing his wife during the first winter, Winslow became the first groom of New England when he married Susannah White in 1622.  He played an important role in the early years of Plymouth Colony.  Serving as Foreign Relations Secretary and agent for the colony, he made frequent voyages to England to plead the colonists' case, secure funds and acquire supplies.  He was elected Assistant Governor of Plymouth Colony in 1625 and Governor in 1636.  Winslow played an instrumental role in securing peace with the local Wampanoag tribe by establishing a relationship with their sachem, Massasoit, even nursing the sachem back to health when he fell ill. 

After being granted land in Marshfield in 1632, Winslow permanently moved his family there in 1636.  He became the founder of the town and of the first church.  He named his large estate after his ancestral farm, Kerswell in Worcestershire, England.  Eventually it became known as "Careswell" and was one of the most important estates in Plymouth Colony.


Winslow continued his journeys to England and never returned from his last trip in 1646 when English Puritan leader Oliver Cromwell appointed Winslow to a series of posts on behalf of the English.  While in England, Winslow had his portrait painted.  It is the only known portrait of a Mayflower passenger.  Winslow died at sea somewhere in the Caribbean in 1655 while serving as Chief Civil Commissioner during the British fleet's expedition to conquer the West Indies.

Josiah Winslow 1628-1680

Edward's son Josiah was among the first Winslow generation to be born in New England.  He grew up in Marshfield at the Careswell estate.  In 1651 Josiah joined his father in London where he married Penelope Pelham in St. Bride's Church, where his father had first become acquainted with the Separatist movement.  Following their marriage, Josiah brought his wife back to Marshfield and the couple settled on the Winslow estate at Careswell.

Josiah's career in Plymouth Colony was extensive.  Militarily, he rose to the rank of Commander in Chief and led troops during the Great Swamp Fight, a decisive battle during King Philip's War.  He was also continuously active in public affairs.  He was first made Governor of Plymouth Colony in 1673, serving continuously until his death in 1680.  He played a prominent role in Marshfield as well.  He co-owned the first grist mill located on the South River and was responsible for the "Major's Purchase," the annexation of a large area of land in what is now Pembroke.

When Josiah died in December 1680, expenses for the funeral were paid from the public treasury in testimony of Plymouth Colony's respect.  Josiah and Penelope were the last generation to live at the original dwelling site at Careswell.

Isaac Winslow 1671-1738 ~ "The Builder"


Isaac Winslow was born in 1671, just nine years before the death of his father, Josiah.  Following in the footsteps of his father and grandfather, Isaac attained numerous prominent positions, both military and civic.  He rose to the rank of colonel in the militia and held many political posts, including in the Colonial Massachusetts House of Representatives and the Plymouth County Court.  He was Chief Justice of the Court of Common Pleas from 1729-1738.

Isaac married Sarah Wensley in 1700. It was right around this time that Isaac had the Winslow House built.  At that time, First Period architecture was just beginning to transition to the Georgian style, which became more common throughout the 18th century.  The house has been compared to an English manor house with its high ceilings and spacious rooms.  The massive clustered-stack chimney allows for five large fireplaces, three downstairs and two upstairs.  The most striking interior feature of the house is the Jacobean front stairway with acorn pendants and large newel posts. 


Isaac and Sarah raised six children in the house, the largest family to live there.  In 1724/5 Isaac deeded part of his farm in Marshfield to his son John and the other part to his son Edward.  After Isaac's death in 1738, his widow continued to live in the house, leasing it from her son John.

John Winslow 1703-1774

John Winslow, son of Isaac and Sarah was among the first generation to be born and raised in the Winslow House.  Upon his marriage to Mary Little in 1725, John settled with his wife into a house in Plymouth, where they remained for 20 years.


Like his forbears, John was prominent in the American Colonies.  He had an outstanding military career, serving in the highest positions afforded in the Massachusetts colonial militia and was a major general by 1756.  His most famous military action was in Nova Scotia during the forced exile of French Acadians, which Henry Wadsworth Longfellow memorialized in his poem, Evangeline.  The French population (Acadians) of Nova Scotia had become British subjects under the 1713 Treaty of Ultrect but refused to abandon their loyalty to France.  In 1755, the British commenced a plan to evict Acadians from their homeland and redistributed among the lower British colonies.


John Winslow was disturbed by these events and wrote, "This affair is more grievous to me than any service I was ever employed hurts me to hear their weeping and wailing and gnashing of teeth."  Winslow brought two French families back with him to Marshfield where the town took the responsibility of housing and caring for them.  Marshfield town records show that in 1757 the schoolhouse was used for the "French people brought to this town." 

In addition to his military career, John served many political roles as did his ancestors.  He served in the Massachusetts House of Representatives and like his father, he was Chief Justice of the Plymouth County Court of Common Pleas from 1762-1774.

John retired from the military in 1757 and moved his family into the Winslow House.  It was John and his wife Mary who oversaw the extensive Georgian renovations to the house in the 1750s.  The couple often hosted friends and neighbors at their "farm" at Careswell.  Mary died in 1772 and John remarried to Bethiah Johnston but only lived two more years, dying April 17, 1774.  

Dr. Isaac Winslow 1739-1819


John and Mary's son Isaac was born April 27, 1739.  Unlike his Winslow ancestors, Isaac did not achieve fame on the battleground.  He instead became a well-respected doctor, apprenticing under Dr. Benjamin Stockbridge of Scituate, whose daughter Elizabeth Isaac later married.  After the death of Isaac's mother and the removal of his father to Hingham with his new wife, the Winslow House was leased to a cousin of the family, General Joshua Winslow, and his wife and daughter 1n 1774.  Isaac and Elizabeth probably moved into the house in the 1790s.


Known as a highly skilled horseman, Isaac travelled the south shore on horseback to visit patients.  He is also said to have walked through snow in snowshoes to see the sick and injured.  Dr. Winslow kept a detailed account book which is now on display at Pilgrim Hall in Plymouth.  In it, Isaac is shown to have accepted household goods such as eggs in payment for his services from those who could not afford monetary reimbursement.  

Though Isaac maintained British sympathies during the Revolutionary War, he and his home remained unmolested throughout the war while other Loyalists saw their homes and land confiscated by the General Court of Massachusetts.  According to tradition, this is because of the high regard held for Dr. Winslow by the local community.

After Isaac's wife Elizabeth died in 1801, he remarried to Frances Gay and continued to live in Marshfield until his death in 1819.  His son John inherited the Winslow House but because Isaac died heavily in debt, John was forced to sell the house and no Winslow has owned or resided in the house since.

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