Henry Wolcott Sr grave

Henry Wolcott Sr.’s 1655 grave in Palisado Cemetery, shown in 2017. He and his wife Elizabeth died within two months of each other, and their joint chest grave (her inscription is on the other side; see photo below) are among the mere handful of extant 17th-century graves in Windsor. Photo by Michelle Tom.

Much has been written about Windsor founder Henry Wolcott. He was an important figure in the town’s early history. But what was his life really like? How did his early years in the colonies contribute to the successes of his descendants? Henry was a man of strong religious convictions, but also a shrewd businessman, born into a family of other shrewd businessmen, who built upon the successes of his ancestors in order to help children and grandchildren build an American dynasty. Two of Henry’s children, Henry Jr. and Simon, exemplify his legacy.

Henry Wolcott, the founder, was baptized in Lidyard St. Lawrence, Somersetshire on December 6, 1578. Though most of the family were fullers and clothiers, Henry was the son of John Woolcott (1547-1623) who ran a gristmill at what is now Watersmeet Farm. The family gained prosperity and respect until Henry’s brother, Christopher, had amassed enough wealth to purchase their father John’s lands from the lord of the manor, making it a freehold. As a child, young Henry enjoyed “a comfortable country life and its pursuits.” Judging by the books in his probate inventory, he was also well-educated, and since he passed these books down to his children, he must have seen to it that they were well-educated as well. Henry acquired lands of his own, and married Elizabeth Saunders, daughter of another family of prominent clothiers, at the Church of St. Lawrence in 1606. All seven of the couple’s children were born in England.

Elizabeth Wolcott grave

Elizabeth Wolcott’s 1655 grave inscription, surrounded by elaborate table top and chest grave markers of her prominent children and grandchildren. | WHS collections 2017.1.51

Emigration to New England

Henry experienced a radical conversion to Puritanism after encountering the minister Edward Elton. After a 1628 reconnaissance voyage to New England, Henry decided to sell a majority of his holdings in England and became a leading figure and financial partner in the voyage of the Mary and John. Henry and Elizabeth sailed with three of their sons, Henry, George, and Christopher. Their eldest son, John, remained in England permanently. Daughters Anne and Mary and youngest son Simon stayed behind as well, but followed their parents to New England a few years later.

In becoming a primary funder of the voyage of the Mary and John, Henry bought himself significant alliances with other powerful men including Roger Ludlow, Edward Rossiter, and Israel Stoughton. They were also leaders of the voyage and would become leaders in colonial Dorchester, MA and Windsor as well. In Dorchester, as you’d expect, Henry parlayed his social capital into positions of power, becoming a freeman and serving as assessor, fenceviewer, and selectman.

It was in Windsor, where he moved in 1636, that he attained his full power. Settling in the area of what is now Island Road, his neighbors were the town’s prominent West Country immigrants. He became the town’s first constable shortly after his arrival. The following year, he was appointed a deputy of the general court in Hartford, and served as a magistrate from 1643 until his death in 1655. In this role, he would have presided over the courts, including the trial of Windsor’s Alse Young, who became the first Connecticut resident convicted of witchcraft in 1647.

Famous Descendants

Oliver Wolcott portrait

Oliver Wolcott Sr., Henry Wolcott Sr.’s great grandson, Connecticut governor, and signer of the Declaration of Independence. Portrait by painter Ralph Earl. Courtesy of the Museum of Connecticut History.

Thanks in large part to their father’s elevated standing, Henry’s children achieved social success as well. Henry Wolcott Jr. was appointed an assistant to the Royal Charter, making him a magistrate, just like his dad. Simon, father of Governor Roger Wolcott and grandfather of Declaration of Independence signatory Oliver Wolcott, fulfilled the family’s military obligations, becoming a trooper in the Connecticut Horse Brigade, and later a selectman and captain of the militia of the fledgling settlement at what is now Simsbury. There, he, like his father and Henry Jr., was a merchant, and was granted license to sell spirits before there was an ordinary established in the area.

It wasn’t all smooth sailing for Henry Wolcott, Sr. Around 1640, following the death of his brother Christopher in 1639, he returned to England, having inherited the family’s landholdings there. Henry had entered into a partnership with Thomas Marshfield of Windsor and Samuel Wakeman of Hartford to purchase interests in the voyages of two ships, the Charles of Bristol and the Hopewell, of London, across the Atlantic with supplies and colonists. Henry probably sailed in one of them. These ships turned out to be losing investments. The voyages were delayed and overcrowded, resulting in extensive lawsuits. Marshfield fell into financial trouble. Though he appears to have escaped blame himself, Wolcott was appointed receiver of Marshfield’s debts and spent 10 years sorting out the difficulty, selling Marshfield’s estate, and dividing up the proceeds. Nonetheless, Wolcott turned even this setback into personal advantage. Wolcott was granted 17 acres of upland and six acres of swamp as payment for settling Marshfield’s debts.

Just like their ancestors in England, the American Wolcotts were geniuses at amassing lands and turning those lands into wealth and status. At his death, Henry Sr.’s estate was valued at over £764, with nearly half of that value in land. He owned nearly 600 acres spread throughout Windsor, along both sides of the Connecticut River, and into what is now Simsbury. That was on top of his inherited lands in England, which he oversaw as an absentee landlord. On his Windsor lands, the family raised cattle and farmed. There is no doubt that Henry’s children benefited from these landholdings, which they inherited, built homes and farms upon, and added to throughout their own lives. The Wolcotts relied on the labor of enslaved Africans, and possibly Native Americans, to manage their holdings.

Wolcott’s 17th-Century Chest

Wolcott family chest

17th-century chest, attributed to Thomas Barber Sr. for Henry Wolcott’s family. Photo by William Hosley.

In January of 2020, Windsor Historical Society was an underbidder on a joined chest, attributed to Thomas Barber, Sr., which is said to have been passed down in the family of Henry Wolcott Sr, through Simon’s heirs. In Henry’s lifetime, it would have been a possession which was symbolic of their status as Connecticut River Valley elite, and was one more trapping of inherited wealth passed down through the generations. At first, in inheriting furniture, the Wolcott descendants could have preserved more of their wealth, rather than using it to purchase new furniture. Furthermore, the chest would have symbolized the family’s network of social alliances. Though Thomas Barber, Sr., lacked the social standing of the Wolcotts, his son, another woodworker, Thomas Barber, Jr., settled Simsbury alongside Simon Wolcott and attained his own enhanced social standing there as a housewright. Later on in the family’s history, the then antique chest became a symbol of their family’s early acclaim and of ancestors which were a source of pride to succeeding generations of Wolcotts.

The Wolcott family, through inheritance, business acumen, and social aplomb, rose in just a handful of generations from being tenant farmers in England to political elites in America. Henry Wolcott Sr., has been described as “the most prominent member of the Windsor settlement throughout his long life, and its richest citizen.” He made sure his children and grandchildren could capitalize on his success, building wealth and attaining status in their own right.


By Kristen Wands, curator, 2020