Charles and Philadelphia “lived on North Mountain, in Augusta Co, VA about 20 miles from Staunton, and were related to the Gatewoods and Lamptons (tradition). About 1805 they removed to Rockcastle Co, KY, where the last 6 perhaps more, of their children were born. Charles had a brother James, it is said, who lived with or near him, and when two of CHarles’s daughters married Wilson brothers james was greatly incensed at his allowing them to marry ‘tories.’ Charles died Nov. 22, 1846. Most of his children went to Illinois. Children, from William Lampton Stuart’s bible”
The speculation as to who was Charles Stewart's father is on D317 (of the ‘SCM’ Stewart Clan Magazine) as well. Here's the whole paragraph:
"Charles Stewart signed a bond 1 Oct 1796 in Madison county, KY, to marry Delphia Simpson, and his fellow bondsman was Matthew Brown. Delphia was born 10 Oct 1777, a daughter of Charles and Ann Simpson. This is revealed in a consent in the marriage bond: 'This is to certify that we are both satisfied that Charley Steward should be married to our daughter Delphey Simson. Given under our hands this 1st day of September 1796. Charley Simpson, Ann Simpson. Teste: Saml Arbuckle, Matthew Brown.' Delphia's sister Peggy married 31 Aug 1796 James Shackelford, and Roger Shackelford married 1 April 1796 Elizabeth Stewart, daughter of Benjamin. This leads to the supposition that Charles Stewart was a son of Benjamin, and this is strengthened by the fact that Charles and Delphia named a son Benjamin, born 20 Sep 1809. They were said to have been married in Virginia, but the record here given shows they were married in Kentucky. The Simpsons were apparently an early Madison County family, as Solomon Simpson married (bond 24 Oct 1792) Sarah Boone, George Boone being his bondsman. James Simpson married 24 Mar 1808 Eleanor Campbell. Charles and his family later resided in Rockcastle county, which is just south of Madison.",
EARLY MARRIAGE RECORDS OF MADISON COUNTY, KENTUCKY
Stewart, Charles Simpson, Delphy pg 28 Oct 02 1796
EARLY MARRIAGE RECORDS OF MADISON COUNTY, KENTUCKY
(Transcribed and indexed alphabetically by Charlotte Ramsey)
Simpson, Benjamin Covington, Milly 224 Nov 03 1836
Simpson, Delilah Estes, Elijah 167 Apr 17 1828
Simpson, Delphy Stewart, Charles 28 Oct 02 1796
Simpson, Duk W Chenault, Sally 137 Feb 13 1822
Simpson, Duke W Lipscomb, Louisa 162 Sep 22 1825
Simpson, Elizabeth Foster, James 120 Mar 20 1817
Simpson, Gabriel Shearer, Miram? 191 Feb 21 1833
Simpson, James Campbell, Elener 37 Mar 24 1808
Simpson, James Caldwell, Mary 153 Feb 22 1825
Simpson, John Embry, Alley 77 Apr 27 1813
Simpson, Levi Windsor, Elizabeth 120 Mar 20 1817
Simpson, Lucy Haggard, Dabney 74 Aug 28 1807
Simpson, Mary Jane Moberly, Benjamin 221 Jan 16 1840
Simpson, Mary K Phelps, Thomas 93 Mar 28 1816
Simpson, Miriam Hamilton, Simeon 229 Apr 14 1842
Simpson, Peggy Shackelford, James 28 Mar 21 1796
Simpson, Robert W Dickey, Dorcas 93 Sep 19 1816
http://freepages.genealogy.rootsweb.com/~cramsey/madco_s.htmlSource: Kentucky Marriage Records (976.9/V2km), Page 503, "Stewart, Charles and Delphy Simpson married October 2, 1796". Extracted from Early marriage Records of Madison County, KY, Genealogial Publishing Co., Inc. 1983.
m. Philadelphia Simpson 02 Oct 1796 in Madison Co., KY