A “Touch of Purple” An e-Royalty Thanksgiving Celebration!

A “Touch of Purple” An e-Royalty Thanksgiving Celebration!

e-Royalty celebrates Thanksgiving!

Thanksgiving in America is celebrated on the fourth Thursday in November. In honor of Plymouth Colony. and the roots of our Thanksgiving, we’re sharing the story of a “royal” Pilgrim, Penelope Pelham Winslow. This article originally appeared in the Pilgrim Society Newsletter and, edited and revised by the author, is reprinted here with permission.

A “Touch of Purple”

by Peggy Baker

Director Emerita, Pilgrim Society & Pilgrim Hall Museum
Chronicler, e-Royalty.com

Americans are fascinated with royalty. Novels by Philippa Gregory and Hilary Mantel are on the best-seller lists, and television screens all over the country were tuned into “The Tudors” and the “White Queen.” We avidly read on the Web all about finding Richard III’s skeleton, and the lengthy saga of his reburial. Online communities of interest, such as e-Royalty.com, provide platforms for shared knowledge, humor and just plain fun.

This fascination even leads some to go so far as to desperately search for royal connections for their Pilgrim ancestors. The truth is that the Pilgrims were not of noble birth. And this is far from being a sad situation! The Pilgrims’ heroism can be found not in their bloodlines but in their accomplishments. They were ordinary people who did extraordinary things.

Second generation Plymouth, however, CAN claim a definite royal connection by marriage. The colonist with the very high connections? Penelope Pelham Winslow, daughter-in-law to Mayflower passengers Edward and Susanna (White) Winslow, the wife of Governor Josiah Winslow and, for a time, Plymouth Colony’s “first lady.”

Penelope Pelham Winslow. Courtesy of Pilgrim Hall Museum.

Penelope Pelham Winslow. Courtesy of Pilgrim Hall Museum.

Our Penelope’s immediate family was strongly Puritan. Her father, Herbert Pelham, and her maternal grandfather, Thomas Waldegrave, were among the “Adventurers,” or founding investors, of the Massachusetts Bay Company in 1630. Herbert Pelham was an advocate for the new settlement from afar until 1638, when he sailed to America. At the time, he was a 29-year-old widower.

Sailing with him were four of his children, including 5-year-old Penelope.

Herbert bought a house in Cambridge, which had by then about 60 houses, as well as a meetinghouse, a market and a college (Harvard). Herbert soon married a young widow, Elizabeth Harlakenden, with two small daughters. The entire family moved into Elizabeth’s larger house, where more children were born.

In 1641, 8-year-old Penelope narrowly avoided death. In the middle of a bitterly cold New England December night, the Pelham house almost burned down.

Massachusetts Bay Governor John Winthrop described the dramatic incident in his journal:

“Mr. Pelham’s house in Cambridge took fire in the dead of the night by the chimney. A neighbor’s wife hearing some noise among her hens, persuaded her husband to arise, which, being very cold, he was loath [very reluctant] to do, yet through her great importunity [urging and pestering] he did, and so espied the fire, and came running in his shirt, and had much to do to awake anybody, but he got them up at last, and so saved all. The fire being ready to lay hold upon the stairs, they had all been burnt in their chambers, if God had not by his special providence sent help at that very instant.”

John Winthrop, Governor of Massachusetts Bay, Penelope’s first New England home. Courtesy of the National Portrait Gallery, Smithsonian Institution.

John Winthrop, Governor of Massachusetts Bay, Penelope’s first New England home. Courtesy of the National Portrait Gallery, Smithsonian Institution.

The Pelham family endured additional comment and excitement when Herbert’s 22-year-old sister Penelope (our Penelope’s aunt) married the newly widowed governor of Massachusetts Bay Colony, Richard Bellingham. The scandal arose because Aunt Penelope was engaged to someone else at the time. In addition, no banns for her precipitous marriage to Bellingham were posted, and Bellingham – as magistrate – conducted his own wedding ceremony. This was strictly illegal. When Bellingham was prosecuted for breaking the law, however, he presided over his own case and declared himself not guilty. Sometimes, even in the 17th century, love did conquer all!

Scandal aside, the political connection with the Governor of Massachusetts Bay Colony served the Pelhams well. In December 1643, Herbert was appointed the first treasurer of Harvard. John Winthrop wrote:

“By order of the general court all the magistrates and teaching elders of the six nearest churches were appointed to be forever governors of the college, and this day they met at Cambridge and considered of the officers of the college, and chose a treasurer, H. Pelham, Esq., being the first in that office.”

Two years later, Herbert was named an Assistant to then Governor Thomas Dudley.

In 1646, Herbert Pelham returned to England. It should be noted that Herbert, even while living in America, had continued to hold family lands in England and Ireland and, upon his return to England, he continued to hold title to land in Sudbury, Massachusetts.


Traveling to England on the same ship as the Pelhams was a Plymouthean who would someday become Penelope’s father-in-law: Edward Winslow. Edward and Herbert were acquainted. Herbert had witnessed a letter written by Edward to Governor John Winthrop of Massachusetts Bay in 1644. Several years later, Herbert and Edward would once again work together (this time in England) on behalf of the United Colonies of New England and in founding the Society for Propagating the Gospel in New England.

Did Penelope accompany her father and the rest of the Pelhams when they sailed to England? Accepted wisdom has always said that 13-year-old Penelope did, indeed, travel with her family. British historian Rebecca Fraser has, however, recently uncovered a document in the English National Archives that indicates that Penelope remained in New England when her father, stepmother and siblings set sail.

In 1683, the widowed Penelope made a deposition in a lawsuit regarding a legacy from her English grandfather’s estate. In that deposition (with the pertinent two words highlighted), she says

Your said orator having lived at the time of the making of the said [will] and ever since in New England” (“Penelope Pelham and a Taste for Litigation, by Rebecca Fraser, The Mayflower Quarterly, September 2015).

Even though “our Penelope” continued to live “ever since” in New England, as this document attests, she would not have been left there unsupervised or without resources. Her aunt, Penelope (Pelham) Bellingham, might have taken Penelope into her household.

Penelope’s life (whether in England or New England) would have centered on her education. She would have been taught the skills needed by an upper-class gentlewoman: to manage and supervise a large household, to raise a family in an effective and godly manner, and to be a gracious partner to a wealthy and properly ambitious husband. Penelope probably also had a tutor and would have learned not only to read her Bible, but also to write and to do accounts.

And at some point Penelope met Josiah Winslow. Josiah, born in 1629, was the oldest surviving child of Edward and Susanna White Winslow (both Mayflower passengers). He attended Harvard in the late 1640s. If he had visited the College earlier with his father, he just might have met the very young Penelope. If there was such a meeting, however, no record of it remains. We know now that the teenage Penelope remained in Boston, creating more likely opportunities for her and Josiah to become acquainted.

However and whenever or wherever it was that Josiah Winslow and Penelope Pelham met, they married in or before 1651. They travelled to “Olde” England where both Josiah’s father and Penelope’s father were living. While in England, Penelope and Josiah had their portraits painted. The two portraits, which hang in Pilgrim Hall Museum, are companion portraits to the portrait of Edward Winslow, which is dated 1651.

The portrait of Penelope Pelham Winslow, 1651. Courtesy of Pilgrim Hall Museum.

The portrait of Penelope Pelham Winslow, 1651. Courtesy of Pilgrim Hall Museum.

When Josiah and Penelope sailed to England, they had not seen their fathers for more than four years. It was to be a final reunion. Josiah and Penelope left England and sailed back across the Atlantic. Edward Winslow and Herbert Pelham never returned to New England. Edward accepted a position in the government of Oliver Cromwell and, while on an official mission to the Caribbean, died at sea off the coast of Jamaica in 1655. Herbert died in his own English bed in 1673.

On Penelope’s return to New England with her husband Josiah, they resided at the family home, Careswell, in Marshfield, Massachusetts, with Josiah’s mother Susanna Winslow. Susanna oversaw a large household. Josiah’s younger sister was still living at home as were many servants and hired hands.

Careswell was a large and gracious house. Josiah’s inventory, taken in 1680, lists the rooms as: parlor, parlor chamber, second chamber, porch chamber, middle chamber, closet, middle kitchen and cellar.

Penelope’s children – a daughter and son who died as infants along with surviving daughter Elizabeth and son Isaac – were born in this house. In this house, Penelope would have entertained and assisted her husband’s public career. Josiah was elected an assistant to the General Court in 1657. He was then elected one of two commissioners to the New England Confederation and, later, Governor of Plymouth Colony.

Josiah died in 1680. He named Penelope, then 47 years old, as his executrix. Penelope had silversmith John Coney of Boston make a mourning ring with a lock of Josiah’s hair. Penelope continued to live at Careswell, raising 16-year-old Elizabeth and 11-year-old Isaac and running the estate. Her daughter married in 1684. Isaac went to Harvard, became a judge and President of the Council of Massachusetts Bay. In 1699, he built a new house on the family property in Marshfield for himself and his mother. The following year, he brought home a bride, Sarah Wensley.

The home built by Penelope’s son Isaac Winslow in 1699, still stands in Marshfield, Mass. Photography by John Phelan.

The home built by Penelope’s son Isaac Winslow in 1699, still stands in Marshfield, Mass. Photography by John Phelan.

Penelope died in 1703, age 70. Isaac’s daughter, born the following year, was named in her honor.

Although our Penelope’s immediate family was very Puritan, her more distant connections were royal indeed. Penelope’s “purple pedigree” was through her father’s family.

Herbert Pelham’s mother (Penelope’s grandmother) was Penelope West (1582-1619). She was one of thirteen children born to Anne Knollys (1553-1608) and Thomas West, the second Baron De La Warr. Anne (Penelope’s great-grandmother) was one of twelve children born to Catherine Carey (1524-1569) and Francis Knollys. One of Anne’s sisters was the great Elizabethan beauty Lettice Knollys who married, first, Walter Devereaux, Earl of Essex and, secondly, Robert Dudley, Earl of Leicester.

Catherine Carey (Penelope’s great-great-grandmother) was the daughter of William Carey and Mary Boleyn (1500-1543), the “other Boleyn girl” and sister to King Henry VIII’s wife Anne Boleyn.

Through William Carey, Penelope could trace a royal line back through Edmund Beaufort, Duke of Somerset (grandson of Katherine Swynford, well-known and well-loved by readers of Anya Seton’s great historical novel) to King Edward III and, from there, back through Edward II, Edward I, Henry III, “bad King John” of Robin Hood fame, Henry II and the spectacular Eleanor of Aquitaine and, ultimately, to William the Conqueror.

Through the royal descent of Eleanor de Berkeley, the wife of Edmund Beaufort, William Carey and his descendants had yet another “royal line” from King Edward I.

An interesting question arises, however. Was William Carey really the father of Catherine? It was well known that Mary Boleyn was a mistress of Henry VIII (before he met her younger, more alluring and much more determined sister Anne). It is likely – or at least possible – that Catherine Carey was, in fact, Henry VIII’s daughter.

Was Penelope a descendant of Henry VIII? Courtesy of the Thyssen Bornamisza Museum.

Was Penelope a descendant of Henry VIII? Courtesy of the Thyssen Bornamisza Museum.

Catherine Carey could, therefore, have been the half-sister of Queen Elizabeth I. This would indeed have been a dangerous bloodline! The Carey children, although strongly similar to the Tudors in appearance and treated with great favor and honor by Elizabeth I, never publicly made the claim.

The question of Tudor descent aside, Penelope was connected to even more ancient lines of nobility through her undisputed ancestress Mary Boleyn. Mary Boleyn’s mother was a Howard and her descent stretches back through the Howard Dukes of Norfolk and the earlier Bohun Earls of Hereford and Essex to King Malcolm Canmore of Scotland and his wife Queen Margaret of Scotland. And Margaret was not only herself a direct descendant of King Alfred the Great, but also a canonized saint!

The Howard Dukes of Norfolk line also led once again back to the English royal Plantagenet line in the person of King Henry III as well as, in the female line, to foreign royalty. Among the forebears of the Howards were King Louis VIII of France and his wife Blanche of Castile, herself the daughter of Alfonso VIII, King of Castile, and the granddaughter of Henry II and Eleanor of Aquitaine.

Penelope’s ancestors also include a number of other colorful figures, including Roger Mortimer, Earl of March, and the infamous lover of Queen Isabella of England (wife of Edward II); William Marshall, Earl of Pembroke (and hero of several recent novels by Elizabeth Chadwick), and Gilbert de Clare, “Strongbow” of Irish fame.

Penelope also had significant American connections, in addition to her uncle-by-marriage, Richard Bellingham, Governor of Massachusetts Bay Colony. Her great uncles were Thomas, Francis and John West. Each of the brothers served, in turn, as Governor of the Virginia Colony. The eldest, Thomas, 3rd Baron De La Warr, is forever memorialized in the state, bay and river named after his title.
Reprinted with permission from The Pilgrim Society and Pilgrim Hall Museum. All rights reserved. Revised and edited by the author, 2015.

Additional Reading

Moore, Susan Hardman. Pilgrims: New World settlers & the call of home. New Haven: Yale University Press, 2007.