From Revolution to the Mayflower: My Surprising Family Tree Journey

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."

The Search for a Patriot

Every family historian has one ancestor who refuses to be found. For me, that ancestor was Levi Allen Leonard. Connecting him to his parents took years of searching through faded records, scattered deeds, and family traditions. What I didn't expect was that the trail would eventually lead to a Revolutionary War patriot named Ezra Leonard.

 

As America approaches its 250th anniversary, my sister challenged me to revisit the Leonard line. After my unsuccessful DAR application through our McDonough ancestors, she wondered if the answer had been sitting in our family tree all along. The Leonards, as I like to joke, have been in America "since dirt." Maybe this was the line that could finally connect us to a Revolutionary War patriot.

 

The challenge of connecting Levi Allen Leonard to his parents stems largely from a single decision he made as a young man—to leave Massachusetts and begin a new life in the South. The paper trail grows remarkably thin after his departure. Only one known birth record identifies a child named Levi Allen Leonard, born on September 28, 1798, in Oakham, Worcester County, Massachusetts, to Levi Leonard and Anna Leonard (despite sharing a surname, there is no evidence that the couple was closely related). Additional support comes from Memorial: Genealogical, Historical, and Biographical, of Solomon Leonard, 1637, of Duxbury and Bridgewater, Massachusetts, and Some of His Descendants, written by Manning Leonard and published posthumously in 1896. In listing the children of Levi and Anna, the author notes simply that "Levi Allen, b. Sept. 28, 1798, went to Alabama in 1819." That brief statement may be the most important clue linking the young man born in Oakham to the pioneer who later appeared in Alabama records. Some researchers have suggested that Levi worked as a surveyor, but by 1824 he had already risen to the rank of captain in Alabama's 3rd Division, 14th Brigade, 21st Regiment. The following year, on June 15, 1825, he married Mary Ann Horne in Bibb County, Alabama. Together they raised seven children, and all evidence suggests that Levi never returned to his Massachusetts birthplace.

 

To better understand Levi Allen Leonard's origins, I turned my attention to his father, Levi Leonard, who was born on July 27, 1776, in Massachusetts. Family accounts seemed straightforward enough. His grandson, Ezra A. Leonard, the son of Rev. Silas Leonard, described him as a surveyor and teacher. Yet the records told a more complicated story. The 1850 census listed Levi's occupation as a "turner," with his industry recorded as "miscellaneous wood products." An 1840 Berkshire County deed added another layer to the puzzle, documenting the sale of "...a certain Turning Factory laying in said Adams below Richmond and Holly Cotton Factory..." to his sons, Ezra and Alvin. The deed was witnessed by another son, Milo H. Leonard. These discoveries made me question whether I was following the correct Levi Leonard. To resolve my doubts, I returned to the records of Worcester County, where most of his children had been born. There I found earlier evidence supporting the family tradition that he had indeed worked as a surveyor. One particularly exciting find was a map titled Plan of Florida, Massachusetts, created by Levi Leonard in 1830 and preserved in the Digital Commonwealth Massachusetts Collection. The map provides tangible proof of his surveying work and, perhaps most remarkably, may preserve an example of Levi's own handwriting. The town of Florida, which he surveyed, is located in Berkshire County, Massachusetts.

 

The Town of Florida lies on the Hoosac Mountain and is from 1000 to 1300 feet high Scant Room for a road between the river and Mountain except 2 or 3 places for small farms and estimated to be three quarters woodland the Town is plotted on a Scale of one Hundred Rods to an inch by 

Levi Leonard Surveyed in Nov 1830

Zadock King Agent for Said Town

Levi's father, Ezra Leonard, was born on July 7, 1750, in Raynham, Bristol County, Massachusetts, to Josiah Leonard and Hannah Campbell. Located about 32 miles south of Boston, Raynham was one of many New England communities whose residents would soon find themselves caught up in the struggle for American independence. Ezra was more than just another name in a genealogy chart. He was a yeoman farmer, an independent landowner, a husband, a father, and a member of the local militia. In colonial New England, yeomen formed the backbone of many communities, enjoying a respected social standing and the right to participate in local government and civic affairs. After a long life, Ezra died intestate in Oakham, Worcester County, Massachusetts, on October 3, 1830.

One year later, a seemingly routine land deed provided a major breakthrough in my research. At first glance, it appeared to be little more than an ordinary property transaction settling Ezra's estate. As I carefully read through the document, however, I realized it contained something far more valuable—a list of his heirs. There among the names was Levi Leonard, my fourth great-grandfather. With a single document, the connection between generations became much clearer, providing crucial evidence that helped link my Alabama Leonard family back to their Massachusetts roots.

Leonard, Ezra et al

to

James C. Fairbank

 

Know all men by these presents that we Ezra Leonard of Gloucester in the County of Essex Clerk and Daniel Cutler in right of my wife, and Olive Cutler wife of said Daniel in my own right both of Grafton in the Worcester, and Elizabeth Leonard of Oakham in said County of Worcester widow and Elizabeth Leonard 2^d of said Oakham spinster, and Levi Leonard of Savoy in the County of Berkshire Yeoman in consideration of two hundred and fifty dollars paid us by James C. Fairbank of Oakham aforesaid yeoman the receipt whereof we do hereby acknowledge do hereby grant all and quit claim unto the said James C. Fairbank his heirs and assigns, all our right, title claim and demand, in and unto all the real estate whereof Ezra Leonard late of Oakham deceased, died seized of situate in Oakham aforesaid consisting of three adjacent lots, bounded as follows to wit one lot of eighty two rods with a dwelling house thereon, bounded southerly by the Rutland & Brookfield County road easterly by a town road, northerly and westerly by land of James C. Fairbank - Also one other lot of land containing sixteen acres and one hundred and seventeen rods with a barn standing thereon, bounded easterly by said town road, southerly by land of Fabian Tomlinson, westerly by land of Eli Burt,northerly by land of said Burt in part and partly by land of Parley Packard and partly by said County road - Also one other piece of land containing ten acres and thirty three rods bounded northerly by land of William Waer, easterly by land of Daniel Rawson southerly and westerly by said town road - To have and to hold the same to the said James C Fairbank his heirs and assigns, to his and their use and behoof forever. And we do covenant to warrant and defend said granted and quitclaimed premises, to the said James C. Fairbank his heirs and assigns forever against the lawful claims and demands of all persons claiming by or under us. In witness whereof we the said Ezra Leonard have hereunto set our hands and seals this ninth day of July in the year of our Lord one thousand eight hundred and set our hands and seals this ninth day of July in the year of our and thirty one 

Signed sealed and delivered in presence of us           }                 Ezra Leonard

James Allen, William Ware                                                           Daniel Cutler

William Ingraham, Eliza Ingraham,                                             Olive Cutler

Berkshire SS October 17, 1831.  Then the above       }                Elizabeth Leonard

named Levi Leonard acknowledged the                                       Elizabeth Leonard 2^d

above instrument to be his free act and deed.            }                Levi Leonard

 

Before me William Ingraham, Just of Peace

Worcester ss . October 11^th, 1831, Personally appeared Ezra Leonard, Daniel Cutler,Olive Cutler, Elizabeth Leonard and Elizabeth Leonard 2^d and and acknowledged the foregoing instrument by them subscribed to be their free act and deed. 

Before me          James Allen Jus. Peace. 

Recd Aug . 21 1832 at 6^h30^m PM Ent^d & Es^d By Art^s Ward, Reg^r

 

One of the most exciting discoveries was Elizabeth's Revolutionary War widow's pension application dated July 8, 1837.  We learn that she married Ezra on April 24, 1775, and that he often employed a substitute for his duties while serving in Captain John King’s company from Raynham.  The narrative allows us to hear her voice nearly sixty years after the Revolution. At eighty-three years old, she recalled hearing cannon fire while her husband answered alarms along the Rhode Island coast. It is a rare and vivid glimpse into the anxieties faced by families during the war.

 

Caleb Packard appeared before the court on her behalf and mentioned that Elizabeth was living in his home and brought an “ancient family bible” with her.  He provided a copy of a page written in her handwriting of the following:

 

"Ezra Leonard married with Elizabeth Campbell. April 2, 1773. He aged 23 & she 19. 

Ezra Leonard Junr. was born Sept. 17, 1774 

Levi Leonard was born July 27, 1776 

Katherine Leonard was born March 20, 1778 

Elizabeth Leonard born November 7, 1780 

Olive Leonard born May 3, 1784 

Katherine Leonard died October 4th, 1828, being in 50 years old. 

Ezra Leonard her father died October the 3, 1830"

 

Seth Dean, an 80 year old from Raynham in Bristol county sent a statement, “…that I was acquainted with Ezra Leonard of Raynham before the Revolutionary War.  That in the Spring of 1775, I enlisted and served as a soldier in Capt. John King’s company in Col. Walkers Regiment eight months at Roxbury in the vicinity of Boston and Ezra Leonard of Raynham served as a soldier in the same company with me all of that time being eight months.  He was married to Elizabeth Campbell of Middleborough before the service aforesaid and they continued to reside at Raynham until the close of the Revolutionary War and then moved to Oakham in this state as I have been informed.  I have lately heard of his death and that his widow is now in full life and resides in Oakham aforesaid.”

 

As the United States approaches its 250th anniversary, I find myself thinking about Ezra and Elizabeth Leonard. Their lives bridged the birth of a nation and the opening of the American frontier. Levi carried the family south to Alabama, where future generations—including my own—would take root. What began as a search for a DAR connection became something more meaningful: the rediscovery of a family's journey through American history.  I close this story with John Hancock’s quote:

 

“Resistance to tyranny become the Christian and social duty of each individual.”

 

Note: I would like to thank my distant cousin Ola Humphries (a 4^th cousin who descends from Levi and Mary’s son, Jessie Milton Leonard).  I discovered her family tree on Ancestry.com in 2011 and it helped piece together The Leonard ancestry.