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Dear Brittany--most everything I have found shows that Dr. John McC's boys, John and James 'left Virginia early'. I have been able to trace them into what is now Berkeley & Jefferson Cos, WV (VA til after 1863-so don't look for pre 1863 WVA records) A James McCormick [father unknown but there were bookoos of McCormick's in this county at this time] who died in 1841 in Clarke Co., VA and mentions a son Charles who is in Ind. In 1850 Charles (Bc1798, VA) is living in Charlestown, Clark Co, IN with a Mary McCormack aged 75-B Va living with him and his family. In the 1860 Clark Co, IN census is a Thomas J. McCormack, aged 40-B IN who has a son Charles F. aged 14, so born c 1844.That's as close as I can come to any Charles McCormick/McCormack.
Now also know that there was the family of Cyrus McCormick (the McCormick reaper man) down the Valley in Rockbridge Co., and they used quite a few of the same names, lived in VA in the same times, and also had famiy who moved West. Have never been able to connect this family & Dr. John, but the families always called each other 'cousin'(which is par for the course in the Shenandoah Valley).
There would be about 3 generations between what you know and what comes down from Dr. John, so get as much info as you can on the folks you know about before you jump into the way-back info and try to connect it. You can go down many false trail trying to come forward rather than documenting backwards. Hope this has been of help. Mary Morris, Archivist, CCHA