As I have written before in this collection: One can get caught up in the search of surnames handed down from one man to the next and miss some awfully interesting people in the generations of women who are equal part of any tree. For a case in point: I have been so caught up in tracing the Smiths, Stilleys, Davis and Van Couwenhovens that I have neglected what often appeared to be some very intriguing family names in their own right: Simpson, Kincheleoe, Taylor and Montgomery to name but a few.  Of these four, the Montgomery family is the oldest family name to be found, thus far, in my tree. It is also the longest running branch of our tree dating back to the centuries prior to William the Conqueror and the Norman invasion of 1066.

The Montgomery line terminates in my tree with the marriage of Matilda Montgomery and Peter Smith, early settlers in Posey Township, Indiana. Peter was born on a Caswell County plantation on Hogan Creek in North Carolina. The plantation once considered one of the premier homes in North Carolina was previously owned by his grandfather Peter Smith, who spent his youth on Bull Run in Virginia. Peter’s father, George Rudolph Smith (one of the younger sons in Peter Smith’s Caswell County clan) left Caswell County with his wife, Lydia Tate, and a number of his neighbors, relations and friends. Lydia and George established a frontier home in Kentucky. Lydia passed away in Kentucky and George prospected his way north into Indiana with his son Peter in tow. George Rudolphus Smith met up with Sarah Armstrong and began a new life for himself.  The Armstrong family was part of the migration pattern. These families were perpetually in search of more land, greater freedom and economic prosperity, among other things.

The Smiths find themselves traveling at each step of the way with Simpsons, Kincheloes, Davis and Montgomery clan members. My great great grandmother, Matilda Montgomery appears to have been born in 1808 in Lincoln County, Kentucky. As Abraham Lincoln was born in 1809 it is clear the county was not named after Abe, but rather a Revolutionary War general, Benjamin Lincoln.  Abe and Benjamin, while generations apart, shared ties to the Lincolns of Hingham, Massachusetts. Our family history also includes ties to Hingham and the Lincoln family. Lincoln County KY lies in the center of the present day state and was one of three counties that composed the original Kentucky. Lincoln County and the two others, Fayette and Jefferson, were separated from Virginia in 1792 and the Commonwealth of Kentucky was born.

Our Matilda was the daughter of James Montgomery (1783-1826) and Nancy Cook (1784-1850). The Montgomery family is well documented in the annals of American and British genealogy. A century old text, The Montgomerys and Their Descendants, by D. B. Montgomery, has proven quite useful in my groveling for information.  The book was published by J.P. Cox in Owensville, IND in 1903. That Cox family name follows the Smith clan for several centuries and I have come close, at times, to proving that my brother in law, Charles Linten Albert Cox, descends from these folks. If I could prove it then I think I would have to accuse Charles of the ultimate example of stalking my sister through the centuries. But that it is a story for another day. Anyone seeking to connect with J.P. Cox for copies of the text will be hard pressed to find him answering his phone. I believe he checked out a long time ago. But his work can be found at the above link.

D.B. (on page 177 of his family journal) tells us that Matilda was the second of James Montgomery’s children. She married Peter Smith in 1825 when she was all of 17 years of age. She immediately turned into a machine capable of turning out babies on a continuous basis, thirteen of them in all and each recorded by name by our family friend and relation, D.B. Montgomery.

Not all of Matilda’s children made it to adulthood, but those that did continued their parent’s propensity for creating life.  Not to slight the other twelve children, but I will turn your attention immediately to child number 12, who was apparently Presidential in stature, as his name was James Monroe Smith, and he is my great grandfather. I have taken the time to list the other twelve children on a separate page and other relevant information related to their earthly travels and offspring. All are Smiths by virtue of having Peter for a father but I am more interested in moving back in time among Matilda’s Montgomery clan harbored in the hills of Kentucky, Virginia, Scotland and Wales and some times Ireland and England.

James Montgomery, Matilda’s da (Celtic for father), was the son of Samuel Montgomery (1743-1815) and Mary Polly McFarland (1753-1819). The McFarland clan is also well documented through the centuries. James Montgomery’s wife, Nancy Cook, was the daughter of David Cook (1755-1824) and Sarah Pullen (1765-1824). David Cook’s father was a reknown preacher Valentine Cook (1730-1791), as was his brother of the same name (Valentine Cook, 1765-1821). Valentine’s mother was Elizabeth Eaton, the great granddaughter of Mayflower pilgrim, Francis Eaton.

Within the Samuel Montgomery generation of our family tree we begin finding the folks whose lives were tangled up in the American Revolution, the pioneers of the Over Mountain territories and the less fortunate in British family wills; wills that gave estates back home to the oldest son and left the remainder of the children to wander the earth in search of new wealth and a rich marriage. Many of the names among this generation of the family tree were major landholders in Virginia in the century prior to the Revolution: Simpson, Wheeler, Taylor, Waddy, Tate, Kincheloe, Anderson, Cook, Pullin, Usher. Many of these families also represented the migration of the Scotch Irish from the Atlantic port cities into the Shenandoah Valley and then either down into the Carolinas, or ‘over the top’ and into the Ohio Valley countryside.

Samuel Montgomery was the son of Hugh Montgomery (1705-1785) and Caroline Anderson (1709-1767). Together they nearly produced a football team, ten children. Seven boys and three girls (that we know of) were born in the span of seventeen years, a feat which kept Caroline in competition for the honor of Mother of the Year. Now this is where it gets a little ‘iffy’ in the family tree. Courthouses were torched during the American Revolution and many records were lost. Folks who like to spend their life piecing together missing links in family trees have kept themselves busy trying to pinpoint which Montgomery descended from one of several brothers who crossed the Atlantic in search of the good life.

Some of us who have more important things to do to occupy our time. I enjoy a good game of sheepshead or a tasting of Wilbur Rancidbatch’s latest draft beer. Folks like me simply take in what others have published and have a go at trying to record something credible in a family pedigree chart. Honesty requires that we also report our fears and doubts about placing ancestors in the tree. It is a bit like recording our notes when we taste Wilbur’s beer.  Honesty is important.

With all due respect to my ancestors, I do know there are consequences if I misplace a grandfather, great uncle or aunt. I have had dreams haunted by cries of ‘incest’ and the bellowing of women who find themselves in bondage to a man who bears no resemblance to what was once their proper husband. These misplaced ancestors threaten me in harsh terms and demand that I put them in their proper place in the tree, and proper bed.

So, we think Hugh’s parents were Robert Montgomery (1687-1779) and Sarah Caulfield (d. 1779). Robert was born in James River in Campbell, Virginia. We know there are several spellings for the Caulfield name and that she appears to be descended from Sir Thomas Caulfield and Anne Moore. If this holds true then she is descended from the Taverner lineage that also produced the likes of William Chaucer, the X Rated author of the bawdy tales of olde England. Robert Montgomery dies in Lincoln, Kentucky County in 1779. Kentucky was a decade away from becoming a stand alone state. This makes Robert Montgomery a pioneer in the annals of Kentucky history, following on the heels of family members like Bailey Smith and putting him in Kentucky a full century before the birth of Matilda Montgomery in 1808. Historical literature from the 1700s refers to Smiths and Montgomerys living and working and intermarrying with Boones, Crocketts, Houstons, Calhouns and Seviers, to name a few of the folks whose tales line the pages of school book history.

Robert Montgomery appears to be the son of one of the three Montgomery men who came to the Virginia Colony. Which of the three men? That turns into a merry go round of hypothetical scenarios that would make for an interesting plot line on a daytime soap opera. Birth records offer conflicting evidence. One document points to William Montgomery (b. 1659), another to James. Both men were identified as living in James River, Virginia.

Both men were the sons of James Montgomery (1627-1689) and Margaret Fitzwilliam (b. 1625). James was an Irishman by birth (Dunskey, Meath Co.) and died in James River. Margaret was a Donegal lass who accompanied James to the New World.

This brief intro to the Montgomery clan covers the North American family from the year 1625 through 1808. The lineage on this side of the ocean when parked in a tree looks like this: Click here.

The tree on the other side of the ocean looks more like a Sequoia compared to the little Oak we constructed in these opening paragraphs. The British tree is documented every step of the way from the year 800 A.D. to the Virginia immigrants in 1625 and can be found in the Thomas Harrison Montgomery’s work in footnote 3. The efforts of D.B. Montgomery were used to construct the American family tree. The European roots take us back to the Norse Vikings and carry us through some characters whose names do show up in the archives of history.

See Page 2 of the Montgomery Clan.

When uncovering such an improbable lineage, as lengthy and clear as this branch, it is important to establish some sources.

  1. Origin and History of the Montgomerys, Montgomery, Bo-Gabriel de, (Name: William Blackwood and Sons, Ltd; Location: Edinburgh and London; Date: 1948;), This book is available electronically on
  2. Montgomery Families: Irish Notes, Montgomery, Robert H, (Name: The New England Historical and Genealogical Register; Date: 1958;), Page 288 Montgomery_Irish_Notes.pdf.
  3. Genealogical History of the Family of Montgomery, Montgomery, Thomas Harrison, (Name: Printed for Private Circulation; Location: Philadelphia; Date: 1863;), Pages 123-127
  4. Montgomerys de Braidstane, Electronic Book .PDF 170 pages, A_genealogical_history_of_the_family_of_.pdf.
  5. Genealogical History of the Montgomerys and their Descendants, Montgomery, David B, (Name: Name: J P Cox; Location: Owensville, Indiana; Date: 1903;;), Electronic Book .PDF 436 pages A_genealogical_history_of_the_Montgomery.pdf   Also: DBMontbgomery Index.doc.
  6. Marriage Notes Hugh Montgomery and Jean Alexander, (Location:;), Notes about the marriage of Hugh Montgomery and Jean Alexander and their home at Mount Alexander.
  7. Ulster-Scots Biographies, Roulston, Dr William and Thompson, Mark, (Name: Ulster Historical Foundation;), Pamphlet # 9.