John married Catherine Russell on 14 Sep 1779 in Virginia, and they were the parents of:
Mary/4 Oct 1788 m. Berryman James
Simon/abt. 1790 - d. in War of 1812

John next married Eleanor Thompson on 5 May 1792 in Mason Co, KY, and they were the parents of:
Martha "Patsy"/abt 1798 m. George McDonald
Benjamin/abt 1806 m. Martha McAlester/McAllister
James/1808
Eleanor "Ellen"/ - d. 1850
Thompson-Thomas/1810 m. Elizabeth "Betsy" Gwinn
Mariah/
John/1811 m. Juliet Renick Davis; 2) Hester Francis
Jane/1819 m. Oliver H. Allen
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Longtime resident of Mason County, Kentucky, which has led many to believe that he was in Mason County when he died. A letter found in the Draper Papers will clear up his discrepancy: "In relation to the death of Uncle John Kenton, I do not know the exact date, but it was prior to 1830 when he was killed in the upsetting of a horse buggy on the south side of Tygart Creek on a hill just above the old Interprise Forge and Furnace, or eight miles from the mouth and about 10 miles from Greenup. I was at the place soon after the accident. One of the neighbors found him a little negro boy who scared the horse that caused the accident." - Dated 19 January 1863. William Kenton Miller

In the Mason County, Kentucky, record is an undated and unsigned sketch of John Kenton which says:
"In 1785 he erected a station on the farm now owned by Dr. Morgan on Kenton's Run. Like his brother Simon, he was a poor manager. Although he owned, at one time a fine estate, he managed before his death to run through most of it. He removed to Scott County in February, 1828. In 1829, he left home to collect certain monies due him and to attend to some ejectments in Greenup County. After a few days he wrote to his family that he had collected some five hundred dollars and was waiting for a further sum which had been promised him. The next word of him was brought to his family by the Sheriff of Greenup County who stated that on the third of July he had been found by someone at the foot of a cliff under such circumstances that led to the conclusion that he had been killed and his body, together with his horse and buggy, had been thrown over the cliff. Whether the murder was committed for robbery, or for the purpose of ending certain land suits was never satisfactorily explained. His wife removed to Missouri on March 16, 1835 and died July 7, 1836."

John Kenton was twice married. He was first married in Virginia on 14 September 1779 to Catharine Russell. The second marriage of John was celebrated 5 May 1792 Mason County, Kentucky, to Eleanor Thompson, daughter of Anthony Thompson and Mary Kelly of Woodford County, Kentucky. Eleanor was also the granddaughter of John and Eleanor Kelly (Deed Book F, Page 32, dated March 1800, Mason County, Kentucky).

Draper Parers 1866 - Mason Arrowsmith states: "Two unmarried daughters of John Kenton, living near Monticello, Missouri." The Draper Papers also gives a reference that the son Benjamin Kenton moved to Missouri.
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"And far to the south, across the Ohio and along the banks of Tygart Creek, birds that had been startled into silence by a sudden loud crash gradually resumed their evening songs, paying little attention to the overturned buggy with one wheel still revolving slowly by its own centrifugal force; uncaring that beneath the buggy lay the crushed and lifeless remains of John Kenton, brother of the frontiersman who had once claimed this very land."
The Frontiersmen by Allan W Eckert, pg. 579