A Great Generation: The Founders of Sandwich, Massachusetts (Part 1)

The people born just before the Great Depression faced a lot of challenges in their lifetimes. Many people spent their lives facing economic hardships, as their parents experienced bank failures, home foreclosures, and job losses. Then, as they became adults, they were thrust into World War II. After overcoming these significant challenges, some have called them “The Greatest Generation.” Tom Brokaw popularized this moniker, thanks to his best-selling book by the same name. But there have been many great generations throughout American history.

If we go back to the early colonization of North America in the 1600s, we find a generation that faced a lot of challenges in their lives. These pioneers left all that they knew to start a completely new life in an unknown land. They and their children also faced a major war, King Philip's War, that wiped out several colonial towns and settlements. But these pioneers managed to establish themselves, forming new settlements, new laws, and new traditions. They were not perfect, but the trials and errors of those first generations led to the creation of a unique system of government in America and new civil liberties for the people. This American example then led to successive revolutions in the practice of government around the world.

Arrival of Winthrop's Company in Boston Harbor (1630) by William Formby Halsall. Winthrop was governor of MA Bay Colony for 12 of its first 20 years

I’m fortunate to call many of those first pioneers in America some of my ancestors. Some of them created legacies of good that impacted their communities. Others probably tried their best, but left stories of misadventure and misfortune. This post and the next includes a mixture of these stories of impact and misfortune from some of my ancestors in this first generation of British settlers in New England.

Thomas Tupper Sr., my 8x Great-Grandfather

First are the Tuppers, who were in my tree in North America for 5 generations, beginning with Thomas Tupper Sr.’s arrival from Sussex, England, in the 1620s. They continued through my great-grandfather Nelson Hughes’ grandmother, Elsie Tupper. While the Tuppers spread widely in New England, my particular line moved to Canada after the Revolutionary War, since Elsie's father was loyal to the English cause. Some of the other Tupper descendants in Canada who are distant cousins include the actor James Tupper and former Prime Minister Charles Tupper (the shortest reigning Canadian Prime Minister in history).

The Tupper House, which stood until the 1920s, when it was burned down by an arsonist

In his early life in England, Thomas Tupper was a shoemaker and leather worker. Then he became a sailor and made his first of at least 3 trips to Plymouth in 1624. His first trip overseas was in 1621 to the West Indies and while onboard, he learned carpentry skills. The second trip was to New England in 1624 and lasted a year as they traded for furs and hardwood. He then seems to have settled down north of Plymouth sometime between 1631 and 1634. It was during these trips that he became familiar with two men who would become important later in his life, Edmund Freeman (another founder of Sandwich) and Thomas Mayhew (the founder of Martha’s Vineyard).

The 10 Men of Saugus

Thomas Tupper is best known as one of the “10 Men of Saugus” who founded the town of Sandwich, the first English settlement on Cape Cod. He is one of 2 of the 10 Sandwich founders I am descended from. Sandwich, MA, is located 20 miles south of Plymouth rock where the Pilgrims landed. These 10 “proprietors” and their families had originally settled in and around Saugus, MA (today known as Lynn). But they were allowed to move to Plymouth Colony in 1637, to establish a new community which they called Sandwich. All together there were 60 families who initially moved to Sandwich.

The court at Plymouth approved this new settlement on April 3, 1637, with a statement reading:

“(it is) agreed by the Court that those ten men of Saugus, viz: Edmund Freeman, Henry Feake, Thomas Dexter, Edward Dillingham, William Wood, John Carman, Richard Chadwell, William Almy, Thomas Tupper and George Knott, shall have liberty to view a place to sit down and have sufficient lands for three score families, upon the conditions propounded by the Governor and Mr. Winslow.”

The Dillingham House, built circa 1659, by the family of one of the 10 Men of Saugus, Edward Dillingham. Photo by Swampyank

At 59-years-old, Thomas was the oldest of the 10 founders. Perhaps because of his senior status, Thomas was active in the running of the early Sandwich town. He was one of the first town clerks. Thomas also represented Sandwich on the Plymouth court, first in 1644 and then for 20 years from 1647 to 1667. He also served on various boards, juries, and committees of selectman, finally retiring when he was over 90. He was also authorized by the colony to conduct civil marriages. And he was very active in the church, serving as a lay minister when the Sandwich church went without a pastor for several years.

Sandwich (MA) Town Hall (1834) and Congregational Church (1848)

His son, Thomas Henry Tupper II, was even more active in civic affairs. Thomas Jr. held positions of town selectman, town clerk, court deputy in Plymouth, representative to the court in Boston, and a lieutenant and later captain of the Sandwich town militia. Thomas also married into a very prominent family when he and Martha Mayhew married. Martha was born in Watertown, MA and was a daughter of Thomas Mayhew, whom Thomas Sr. knew from his time as a sailor.

Martha’s father, Thomas, was initially a trader in Boston before settling in Watertown, MA. A few years later he secured the land rights to Martha’s Vineyard. And after many years there, he was officially appointed “Lifetime Governor” of the island by the British leader in New York.

Martha's Vineyard, which was long a part of New York colony. Edgartown is where the Thomas Mayhew and his son Thomas Jr. began the town

Another extraordinary individual was Martha’s brother, Thomas Jr., who was the first in the family to physically move to Martha’s Vineyard and start building a home and organizing the community. Thomas Jr. was also a pastor, who is known as one of the first missionaries to the Native Americans. His work with the local Wampanoag tribe, that numbered over 1,000, was one of the few examples in New England where the indigenous people kept their culture while also converting to Christianity. The relations between the tribe and the settlers were so good that the island was one of the few places that avoided bloodshed between the Wampanoags and the English settlers in the major rebellion called King Philip’s War.

A stained-glass panel at the Washington National Cathedral. The panel at right depicts Thomas Mayhew Jr. baptizing Hiacoome, a Wampanoag who became a pastor and missionary on Martha's Vineyard. Wampanoags later led services for both their people and the English settlers.

Through Martha (my 7x great-grandmother) and her father Thomas, some celebrities my family is related to includes the George W. Bush, Taylor Swift, Gregory Peck, Bill Gates, abolitionist Lucrecia Mott, 49ers QB Steve Young, filmmaker Ken Burns, and Marilyn Monroe.


A Turbulent Time in New England

Looking back at this period, remarkably, things turned out well for the Tuppers and their associates in Sandwich. During the period from 1636 to 1638, Massachusetts Bay Colony was gripped with a political and theological struggle called the Antinomian Controversy. Essentially, this was a disagreement among groups of Puritans about whether salvation and overcoming sin could be realized through “free grace” or if it had to be earned through “good works.”

When many of the residents in and around Boston began meeting on their own to discuss this and other questions, the colonial authorities decided the government had a right to decide who you could meet with in your homes and what you could talk about. They banished Anne and Rev. William Hutchinson, Rev. John Wheelwright, and several others from the colony. They also warned others to leave or face an examination by their “court.”

That such control of thought, expression, and assembly ever existed in America is hard to comprehend in today’s world. But that is how it was in the early years of the New England colonies. Some people had come to America from England looking for economic opportunities. Others who arrived in Boston were primarily looking for more religious freedom. So, not surprisingly, many from these two camps left Boston in 1637 and 1638 to get away from the excesses of the Puritan theocracy in Boston.

Map of towns in Plymouth Colony with their incorporation dates. Sandwich, MA was incorporated in 1639

The religious and political upheaval in Boston seems to explain the timing of some people who moved to Cape Cod and elsewhere. Along with the 60 families who went to Sandwich in early 1637, 60 families moved to Rhode Island in late 1637. Then in 1638 there was a similar sized group who went to start a settlement that became New Haven, Connecticut. Other groups spread out to other areas in Massachusetts and New Hampshire, and some even returned to England.

The controversy in Boston probably influenced some in the Sandwich group to try Plymouth colony to distance themselves from the Boston government. But the Tuppers’ move seemed to hinge primarily on connections to his friends and former business associates.

As mentioned above, Thomas had various friends who were active in trading or financing the ships traveling between England and the colonies. One of those friends was William Geere, a friend of Thomas’ father, who was a passenger on the ship Abigail that arrived in Boston from Plymouth, England, on October 8, 1635. Unfortunately, Geere and his wife died of smallpox on the ship as it was quarantined in Boston harbor. Geere bequeathed money to Thomas and four others in his will. These 5 all were among those 10 founders of Sandwich.

Boston Harbor, Sunset, by Fitz Hugh Lane

Another passenger on the Abigail was a “Gentleman” (an official title) named Edmund Freeman. Thomas knew Freeman in earlier years from trading and now the two were reacquainted after the Abigail’s arrival in Boston. Whether this was a lucky coincidence or it had all been pre-planned, 18 months later Edmund Freeman would lead the move of the 10 proprietors and other settlers of Sandwich.

In the next segment, we shall look at the impact and juice that Edmund Freeman, my 9x great-grandfather, had on Sandwich, MA, and Plymouth colony.


Thanks for reading. Until next time.





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