The Dinwiddies & Wilsons have many ties.Among them:
John Wilson born in (Northern) Ireland, was married in 1774 to Mary Dinwiddie (born 1751, daughter of David Dinwiddie V & Jean McClure) at or near Marsh Creek, Adams Co., PA.
David V's grandson Thomas Dinwiddie married Mary Ann Wilson in 1808. Her parents were Robert and Mary Wilson, from Pennsylvania. Thomas & Mary, with their children, migrated to northwest Indiana in the 1830s.
Thomas' daughter Mary (born 1823) married James H. Wilson in Indiana, and they took the Oregon Trail in 1853.
I have no info about the Virginia Dinwiddies or Wilsons.