Samuel Willcockson was a son of John and Sarah (Boone) Willcockson. His mother was the oldest sister of the famed Kentucky pioneer, Daniel Boone. Samuel married Anna Jordan (1756-1840). He lived in the area of Rowan Co., NC until 1775, when he travelled to KY (in the same year that his Uncle Daniel Boone led the expedition to pave the Wilderness Road). In KY, Samuel established a claim to 1,000 acres on Licking Creek, but within a short time he returned to NC. By the 1790s, Samuel had moved his family to present Ashe Co., NC, where he would live until about 1815, when he once again went to KY. This time, Samuel settled in what was Estill County and is now part of Lee Co., KY. After his death, his widow and several of his children moved further west to Fulton Co., IL. It should be noted that there is a discrepancy regarding the date of death of Samuel Willcockson. His gravestone shows his date of death as "NVR 1825". The family bible of his grandson, Isaac Aaron Willcoxson, gives his death date as 16 September, 1825. Estill Co., KY records indicate that both of these dates are likely incorrect. Samuel's name is found on the Estill County tax lists until 1827, and the inventory of his estate was recorded in Estill County in March, 1827. Therefore, it is believed that Samuel probably died in early 1827.

Information provided by his grandson, Jeremiah F. Willcoxen, in the Portrait and Biographical Album of Fulton County, Illinois (Biographical Publishing Company, 1890, pg. 665; 835), describes Samuel Willcockson as follows: "The grandfather of our subject was a farmer. He moved from his early home in North Carolina to Boonesboro, Ky., and was one of the pioneer settlers of that section of the State. He was a broad-minded, large-hearted man of deep religious convictions and was an influence for great good among his fellow pioneers. He was a member of the Regular Baptist Church and he had two sons who were Baptist preachers."

The following interesting article gives information about the grave of Samuel Willcockson.

"A MOUNTAIN MYSTERY"

(Appeared in The Beattyville Enterprise, Beattyville, Ky., May 22, 1952, "Eastern Kentucky Vacation Edition", Sec. 3, p. 4; and in The Powell County Herald, of Stanton, Ky. May 21, 1952.)
"Hardby the building which houses the St. Helen's Grade School in Lee County is an old cemetery wherein the remains of Samuel Wilcockson has rested in peace these 127 years.
"Against this assumption no person has ever voiced a doubt because the stone bearing the date is there to prove it. But as to his sojourn here on earth as an entity is something else.
"What arouses the curiosity concerning the Old Willcockson is his headstone. It is no different from any of the others except that it bears the name, the date of death which the others do not have. This gives rise to the supposition that he must have been a man of some note to warrant the treatment. All the other pioneer graves are marked by flat stones picked up from the nearby field and bear no markings at all.
"Wilcockson's grave is marked by a large flat stone and bears the legend:
"Here Lies The Body of Samuel Willcockson
Born 1755 Died N V R 1825"
"Notwithstanding the spelling the name and date of birth are carved in beautiful and precise Gothic letters. The date of death however is crudely inscribed as if two different persons had a hand in the work.
"Now as to who this man was, what he did, and where he was from is something that probably will forever remain a mystery. Despite repeated investigations no one in St. Helens knows anything more about the man than what is carved on the headstone.
"The Snowdens and McGuires came to St. Helens in 1826 and are understood to be the first settlers. The grave was there when they came and none of them ever knew Willcockson, at least if they did, they never told. Their descendants say the grave was as much a mystery then as now.
"The only clew as to the old man's identity, who came into this world about the time General Braddock was getting a clobbering from the Indians, is the fact that in the archives of the Estill County Court are some old papers showing that a family of Willcocksons were in that vicinity along about that time. But how this man came to die and be buried so far away is another story.
"Willcockson's gravestone has been the source of much speculation. Some believe that he carved all but the date of his death himself and left it to others to inscribe the date of the event which he knew would prevent him accomplishing the task. The fact that the lettering at the last is not so well done as the first, tends to support this opinion.
"But whatever the story may be old Willcockson lies at peace beside the remains of an Indian mound in a grove of age old beeches and the brief record of his life, meager as frontier accounts usually are, adds a mystery incident to the colorful past of Eastern Kentucky." [excerpted from "Wilcoxson and Allied Families" by Dorothy Ford Wulfeck, 1958]