Every family tree has its surprises. Mine began with a Revolutionary War patriot.
While researching my fifth great-grandfather, Ezra Leonard, I discovered enough documentation to consider applying to the Daughters of the American Revolution (DAR). As I worked backward through the Leonard family, I turned my attention to Ezra's mother, Anna Leonard, my fourth great-grandmother.
One question immediately caught my attention: Anna Leonard had married Levi Leonard. Were they cousins? After tracing both families, I discovered they were not related at all. That mystery seemed solved, and I moved on to other branches of my family tree.
Nearly fifteen years later, however, I came across an old note suggesting that Anna Leonard might descend from a Mayflower passenger. The claim sounded almost too good to be true. Like many family stories, I assumed it would eventually fall apart under careful research.
Instead, every generation led to another well-documented connection. To my astonishment, Anna's ancestry reached all the way back to James Chilton, one of the passengers aboard the Mayflower in 1620.
Name | Birth Year | Death Year |
James Chilton | 1556 | 1620 |
Isabella Chilton | 1587 | 1665 |
Sarah Chandler | 1622 | 1675 |
John Leonard | 1645 | 1699 |
Moses Leonard | 1680 | 1775 |
Andrew Leonard | 1719 | 1807 |
Anna Leonard | 1778 | 1864 |
Levi Allen Leonard | 1798 | 1860 |
Milo Washington Leonard | 1842 | 1907 |
Davis Samuel "Dade" Leonard | 1873 | 1944 |
Trentie Alice Leonard | 1900 | 1985 |
Paul Jones Sutton | 1925 | 2010 |
Paula R. Sutton |
Discovering a Revolutionary War patriot in my family was exciting. Discovering that another branch reached back to one of the Pilgrims who crossed the Atlantic more than 150 years earlier was something I never expected.
James Chilton: From England to the New World
James Chilton was born about 1556 and spent much of his life in Canterbury, England, where he worked as a tailor. Around 1600 he moved his family to Sandwich, Kent. Religious conflict soon changed the course of his family's history.
His wife was excommunicated from the Church of England after participating in the private burial of Andrew Sharpe's child, an act that reflected the growing tension between religious dissenters and church authorities.
Seeking the freedom to worship according to their own beliefs, James and his family joined the English Separatists and moved to Leiden, Holland. Although Dutch society offered greater religious tolerance, life there was not easy. Employment opportunities were limited for immigrants, and many English families worried that their children would gradually lose their language and identity.
The Leiden records preserve one remarkable glimpse into James's life. On the evening of April 28, 1619, sixty-three-year-old James and his daughter, Ingle, were attacked by a group of about twenty boys who mistakenly believed they belonged to the Remonstrant movement. Stones were thrown, and James was struck so hard that he fell to the ground. Within a year, James would make the most important journey of his life.
A Voyage That Changed History
In 1620, the Separatists decided to leave Holland and establish a colony in the New World.
Two ships were intended to make the crossing: the Speedwell and the Mayflower. Repeated leaks forced the Speedwell to turn back, and its passengers crowded aboard the already full Mayflower before departing England in September 1620. Of the 102 passengers, James Chilton was the oldest at sixty-four years of age.
The Mayflower was never designed to carry families across an ocean. Originally built as a cargo ship for transporting wine and lumber, it measured only about 100 feet long. More than 100 passengers, along with 30 to 40 crew members, spent sixty-six days packed into a dark, cramped deck with less than five feet of headroom.
It was a miserable voyage.
Mayflower in Plymouth Harbor, painting by William Halsall
Food consisted mainly of hardtack (crackers), dried meat, and beer. Powerful Atlantic storms battered the ship, cracking one of its main support beams. Only a large iron screw carried aboard for construction work allowed the crew to brace the damaged timber and continue the voyage.
When worsening weather made reaching their intended destination near present-day New York impossible, the colonists instead anchored at Cape Cod. Because they had landed outside the jurisdiction of the Virginia Company, the adult men drafted what became known as the Mayflower Compact, agreeing to govern themselves under laws they would create together while remaining loyal to the English king.
By Jean Leon Gerome Ferris - This image is available from the United States Library of Congress's Prints and Photographs
A Heavy Price
The passengers arrived in November 1620 exhausted, hungry, and unprepared for a New England winter. James Chilton never saw the colony flourish. He died shortly after arriving while the ship remained anchored in Provincetown Harbor. His wife followed soon afterward, leaving their thirteen-year-old daughter, Mary, an orphan. Before the first winter ended, nearly half of the Mayflower passengers had perished. Yet the family line continued.
James's daughter Isabella Chilton, my ninth great-grandmother, had remained behind in Leiden after marrying Roger Chandler in 1615. They did not immigrate to Plymouth until 1632, where Roger became a freeman the following year.
Their daughter Sarah Chandler, my eighth great-grandmother, married Solomon Leonard, linking the Mayflower line to the Leonard family that would eventually produce my Revolutionary War patriot.
John Leonard became a respected citizen of Bridgewater, serving in several town offices. An interesting twist in the records led to years of confusion among genealogists. Because land inherited from the Chandler family passed through John, one published genealogy mistakenly identified his wife as Sarah Chandler—impossible, since she was old enough to have been his mother. Careful examination of the records shows that John's wife was another Sarah whose maiden name remains unknown.
Moses Leonard served as an ensign in the colonial militia, operated an inn, and became a respected gentleman in Worcester County. His life spanned the years leading up to the American Revolution, although he died in December 1775 before learning the outcome of the conflict that had just begun.
Andrew Leonard began life as a husbandman, eventually becoming a yeoman. His family worshipped at the Oakham Congregational Church, where the minister's son later remembered their humble home: "built by the side of a ledge of rocks; short logs were used for seats." It is one of the few surviving descriptions that allows us to picture how my ancestors actually lived.
With Anna Leonard, two completely unrelated Leonard families became one. One line traced back to English settlers who would fight for American independence during the Revolution. The other reached back another century and a half to James Chilton, who crossed the Atlantic aboard the Mayflower seeking the freedom to worship according to his conscience.
I began this research hoping to document a Revolutionary War patriot. Instead, I found a story stretching from colonial Massachusetts to the Pilgrims of Plymouth—a reminder that family history often rewards those willing to follow unexpected clues.
As Plymouth Governor William Bradford later wrote of the Pilgrims:
"Their desires were set on the ways of God, and to enjoy His ordinances."



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