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 2d 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 2d
above instrument to be his free act and deed. } Levi Leonard
Before me William Ingraham, Just of Peace
Worcester ss . October 11th, 1831, Personally appeared Ezra Leonard, Daniel Cutler,Olive Cutler, Elizabeth Leonard and Elizabeth Leonard 2d 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 6h30m PM Entd & Esd By Arts Ward, Regr
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 4th 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.
