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Chapter 4

The Journey West


According to old family letters; “in the fall of 1784, James III with his father, James Ware II, visited Kentucky and remained there all that winter.  This was at the time when people lived in stations [forts] (Ref. 6,35G, 334) Cornelia Ware also mentioned the stations in her own letter.  She wrote, “this probably meant a stockade as protection against the Indians.” (Ref. 2)


Photograph and drawing of typical frontier station
Courtesy of the Kentucky Historical Society

She was absolutely right because, as the Kentucky Historical website explains, “. . . in the late 1700s, early settlers to Kentucky had to fight for their survival.  They came from the east to claim the land and build up settlements out of the wilderness.  Life was hard and dangerous.  For many, their best hope for survival was in a fort.  These forts, and smaller structures called stations, were the beginnings of today’s Kentucky towns.” (Ref. 2095)  In 1792, just four miles from Frankfort, a little settlement on Elkhorn was attacked and several family members slaughtered.  (Ref. 2291)  The threat of Indian attacks was very real.  Contrary to common belief, however, the pioneers did not live in the stockades for any great length of time.  It was often the case that “they lived in separate cabins near the forts, and when an Indian raid threatened, they loaded packhorses with household goods, herded together the cattle, hogs, sheep, and chickens, and rushed into the fortification then (Ref. 2254)  Sometimes smaller stations were created between families.

Courtesy of the Hopewell Paris Bourbon County Museum

Dr. Ware returned to Virginia after the winter, but “in 1789, he revisited Kentucky and left his sons, Thompson and James III, there.” (Ref. 6, 35G)  It was decided that the sons would stay in the area and establish roots so that the entire family could later make the move.  Thompson later wrote his niece, Sally Stribling, about how he and James “were raised and educated together until our father took us to Kentucky and there left us.  We got separated; he located at Louisville and I in the neighborhood of Lexington when my age was 20 and his about 18 months younger (Ref. 35E)  Both sons were active in the development of the area.  “Thompson settled near Paris, which later became the county seat for Bourbon County.” (Ref. 299, 845)  James “engaged with Mr. Johnson, the Clerk of Jefferson County, writing in his office until he became fully acquainted with the work.”(Ref. 6, 35G)


Courtesy of the Hopewell Paris Bourbon County Museum

In 1791, James III returned to Virginia to help his parents and the rest of the family prepare for the great migration to Kentucky. (Ref. 6, 35G)  His health was not good, however, and he would ultimately return to Virginia for the remainder of his life.  His assistance with the move was invaluable, though.  “It was a long and dangerous trip made in wagons and by horseback, with all their Negroes and what possessions that could be carried.  They feared the Indians, but were most fortunate in not meeting any (Ref. 2)  They had to be on the alert for Indian attacks on the water, as well as on land, for they sometimes used flatboats for transportation.  Polly would often tell her granddaughter how “her oldest child [Fannie, born Dec. 20, 1791] was but three months old when they came to Kentucky.  They descended the Ohio in flat boats in momentary apprehension of being attacked by the Indians.” (Ref. 174, 602)

The family had every right to be fearful because in the time frame just before their move, from 1783 to 1790, there had been “no less than 1,500 authenticated instances of men, women and children being killed or captured by the Indians in the sparsely settled Kentucky.” (Ref. 904)   The flatboats, built with green timber and put together with wooden pegs, were hardly a comfortable way to travel, let alone being safe. (Ref. 903, 904)  Travelers were warned repeatedly that, “as frequent landing is attended with considerable loss of time and some hazard, you should contrive to land as seldom as possible, you need not even lie by at night provided you trust the current and keep a good lookout  (Ref. 2265)  

  Currier & Ives

The advance preparations made in the earlier years were a huge help for the weary travelers.  “Several of the men had been out before, clearing the land and preparing a shelter for them on land near where the city of Lexington now stands.” (Ref. 3)  One of James’ sons later wrote that his father “had, previous to the move, sent out some Negroes and an overseer to make a settlement and clear some ground on the same place that he lived and died on(Ref. 35G, 299) We do not know exactly how long the journey took, but Charles Ware wrote that the family “moved to Kentucky in the spring . . . and arrived at their new home on the 16th of June (Ref. 35G, 334, 2247)   If, as Polly said, her baby (born in December 1791) was three months old when they began the trip, their spring departure began in March of 1792.  With an arrival date of June 16th, the travel time must have been approximately three months.  Quite an undertaking!

As mentioned before, it was a wise practice for families and friends to move together as a unit and put down roots close to each other; often as immediate neighbors.  This offered safety as well as camaraderie.  The Ware and Webb families were close knit, mainly due to the connection of marriage.  Consequently, they owned properties that were almost side by side.  Another strong tie existed between the Ware and Conn families, probably beginning back in Virginia too.  Thompson’s future father-in-law, Thomas Conn, at one time, “owned about 3500 acres of land on what is known as the Long Mountain Tract on the west side of the north branch of the Rappahannock River, then called the Hedgman River.” (Ref. 740)   Thomas decided to move to Kentucky even before James Ware did, and it was not long before the Wares and Conns were also closely intertwined by marriage.  Thompson Ware married Sallie Conn, William Conn married Fanny Webb (the daughter of Charles and Polly Ware Webb), and James Conn married Kitty Webb (the daughter of Isaac and Lucy Ware Webb.)  Over the years, there would be many weddings between these three families and cousins with similar names would abound in the region.

Shaded area show counties formed from Kentucky County


Pink= Woodford Co.  Blue= Bourbon Co.  Green = Fayette Co.  Yellow = Franklin Co.

Travel route taken by the Wares & Webbs


As Theodore Roosevelt wrote in 1889, “The settlement of Kentucky was a much more adventurous and hazardous proceeding than had been the case with any previous westward extension of population from the old colonies; because Kentucky, instead of abutting on already settled districts, was an island in the wilderness, separated by two hundred miles of unpeopled and almost impassable forest.” (Ref.867)  

It took a hearty breed of people to face this kind of journey, but the Wares made it safely to their new home and quickly started carving out their futures in this new land.  When they left Virginia that March of 1792, James II was 51 years old, Caty 39, their oldest son Thompson 23, James III was 21, Polly 20, Lucy 19, Charles 17, Kitty 15, and youngest child, George, was only 13.  Amazingly, the patriarch of the group, James Ware I, was 78 years old at the time!  They traveled with at least two infants.  We know Polly’s baby daughter was only three months old, and Lucy and Isaac, who had married in December of 1790, also had a baby with them.  Their daughter, Catherine Webb (born in September 1791) was six months old.  To complicate things, Lucy became pregnant again while traveling, but she might not have been aware of it at the time.  She would give birth to her daughter Winny seven months after arriving in Kentucky.  There was a family member from virtually every end of the age spectrum; all willing to battle an untamed wilderness to pursue their dreams.  The children of James and Caty would provide many descendants to carry the Ware name on, but they would raise these children as Kentuckians, not Virginians.



 Supporting Documentation for Chapter 4



      B.  March 13, 1741/2                     B. February 9, 1753

      D.  May 7, 1820                              D. April 23, 1802


Dr. James Ware was the 2nd son of James Ware I and his wife, Agnes Todd Ware.  He studied medicine in Virginia and married Virginia Catherine Todd there in 1767.  He later relocated to Kentucky with his whole family except his namesake, James Ware III.


(1) Thompson Ware – born April 5, 1769            died Sept. 9, 1852

Married Sallie Conn – daughter of Thomas Conn  

(2) James Ware III - born Jan. 13, 1771         died Sept. 13, 1821

Married Elizabeth Alexander on Nov. 10, 1796 and Harriet M. Taylor on March 16, 1808    

(3) Mary (Polly) Todd Ware - born Sept. 4, 1772  died Dec. 29, 1854

Married Charles Webb in 1788   

(4) Lucy Ware - born Nov. 12, 1773         died June 22, 1833

Married Isaac Webb on Dec. 23, 1790  

(5) Charles Ware - born Aug. 19, 1775       died July 1839

Married Frances Whiting on Nov. 29, 1803  

(6) Catherine Ware - born May 1, 1777        died  Dec. 11, 1861  

Married Dr. John M. Scott in 1796

(7) George Ware - born Feb. 9, 1779       died July 28, 1849

Married Nancy Ferguson on June 10, 1812

(Ref 621, 975, 1070)

** See section on “double-dating” to explain the date for James’ birth. 

Chapter 5

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