Squire Boone Chapter 3: Exploring a new wilderness

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By Ron Van Stockum

With all their companions either dead, missing or having headed back home to North Carolina, Daniel Boone and his brother Squire found themselves alone in a vast wilderness, known to them as “Kentucke.”


They hunted every day and spent the winter of 1769-70 in a “little cottage,” in the prose of author John Filson, which was probably, a lean-to, or a primitive log cabin.  On May 1, 1770, a year after the party’s departure from the Yadkin settlements in North Carolina, Squire “returned home to the settlement by himself, for a new recruit of horses and ammunition, leaving me [Daniel] by myself, without bread, salt or sugar, without company of my fellow creatures, or even a horse or dog.”

Squire, too, would have had a feeling of loneliness as he followed the Warrior’s Path through eastern Kentucky, especially dangerous at that time of year, the weather being conducive to the movements of Indian hunters and war parties.

Within a short distance of the settlements, he was surprised and robbed of many of his furs by Indians.

Neal Hammon, an architect and historian from Shelbyville, has described the Warriors Road in the following terms:

“In the beginning there was one main road leading northward from Cumberland Cap to the Ohio.  This was the famous War Road, or Warriors Path, which had been traveled for centuries by the Indians. This trace ran through Flat Lick, Manchester, down the Station Camp Creek to the Kentucky River, and across the central part of the state to the Ohio River.”

Daniel, during the 3-month period when he was alone in Kentucky, or during the 12  months that his only companion was Squire, traveled extensively through the Bluegrass area of Kentucky, observing landmarks and naming streams.

Surely Daniel, alone or in the company of Squire, visited the mouth of Otter Creek on the Kentucky River, where Boonesborough later would be located. It is surprising that historians have not emphasized this fact.


Squire returns

Squire Boone, to Daniel’s “great felicity,” on July 27, 1770, met Daniel, according to appointment, at their old camp on Station Camp Creek.

Shortly thereafter, not thinking it safe to stay there longer, they proceeded to the Cumberland River, reconnoitering that part of the country until March 1771, and returning home to the Yadkin in April.

There are reports from a number of historians that Squire, during this long hunt, may have made a second trip, taking more furs and hides back to the settlements and returning with supplies. 

Lyman C. Draper, during the middle of the 19th Century, assiduously collected manuscripts and other source material relating to America’s westward movement, including interviews with descendants of hunting companions of the Boone brothers.

Included in his collection is a statement that Daniel Boone returned home in 1771, after his two-year absence, to find a child in the cradle.  “Oh well,” he said, “whose is it?” 

His wife, Rebecca, replied, “Why, it’s Brother Squire’s.”

To which Daniel is reported to have responded, “Well, one of the name is all the same.”  This anecdote, called “Boone’s Surprise” in many biographies of Daniel Boone, is considered hearsay and entirely discredited by most Boone historians.

Accepting the dates of this long hunt,as recorded by Daniel in Filson’s “The Discovery, Settlement, and Present State of Kentucke,” and there is no reason to dispute them, we can calculate that, while Squire did not depart with the party on May 1, 1769, he did spend nearly 15 months on this hunt, either alone on the trail or with his brother.


A tragic beginning

In August 1773, Daniel Boone, having sold his farm on the Yadkin, was at Castle’s Woods on the Cinch River, now Castlewood, Va., one of the most westward communities, making preparations to settle in Kentucky.

On Sept. 25, a group of 40 to 50, including the families of Daniel and Squire, departed for Kentucky.  They were apparently under the leadership of William Russell, a prominent resident of Castle’s Woods, with Daniel Boone, not yet well known, as a guide.  The movement by pack train was slow, and it took about 2 weeks to travel the 60 miles to Powell’s Mountain in eastern Virginia.

On the night of Oct. 9, while the main party was still about 45 miles east of the Cumberland Gap, a supply party, 3 miles behind, near Walden ridge in present Lee County, Va., was attacked suddenly by a small force of Indians.

Six pioneers were killed, including Daniel Boone’s eldest son, James, 16, and Russell’s son Henry, who were horribly tortured before being killed.

The sole surviving witness was a member of this supply party who had escaped and was hiding nearby.  He reported that James, recognizing his assailant as Big Jim, a Shawnee, who had been a frequent visitor at the Boone’s farm, called him by name, first pleading for his life and then begging for death.

Ahead in the main party, Daniel Boone, upon hearing of this massacre, sent Squire with a small group back to the site, taking along linen sheets provided by Daniel’s wife, Rebecca, for protection of the bodies from the “cold earth.”

Discouraged, the settlers, after gathering up their cattle, decided it would be too dangerous to proceed with such a small force.

They retreated to Castle’s Wood, and most families returned to their homes in North Carolina.  Daniel and his family, however, remained for the winter in a friend’s cabin near the Clinch River.

Next: Boonesborough