Some decendants of Squire Boone (Daniel Boone's father) married into the Phipps family of Grayson County, but an earlier connection was present. Squire Boone owned property in Rowan County, NC, near the fork of the Yadkin, not far from present day Mocksville, NC. Ephraim Osborne, Captain Enoch's father, and his brother, Caleb Osborne both owned property near Squire Boone. There exists an old map showing both Caleb Osborne's property and Squire Boone's property in close proximity. Click here to see a copy of the map. Note the unusual horseshoe curve of the Yadkin River can still be seen on current maps, just Southeast of Mocksville, Caleb Osborne's property can be seen just Northwest of this bend in the Yadkin. (The Boone's properties are highlighted on the map.)
During the Indian Wars prior to the Revolution, was Lord Dunmore's War from 1773 to 1774. This was a war between the Colony of Virginia and the Indian nations of the Shawnee and Mingo. John Murray, the last Lord Dunmore, the British Royal Governor of Virginia, asked the Virginia House of Burgesses to decalre war on hostile Indian nations and muster a volunteer militia for the campaign. Indians had increasingly been raiding homes of colonists who settled west of the Appalachians, where the Indian nations held treaty rights to hunt.
One such volunteer company was under the command of a Captain Looney, whose mission was to guard the Clinch River frontier, and prevent or respond to hostile Indian raids. Under Looney's command were Lieut. Daniel Boone, and his older brother Israel Boone. From Grayson County were Lieut. John Cox, Sergeant Enoch Osborne, and his brother Ephraim Osborne, Jr. This Sergeant Enoch Osborne would later become Captain Enoch Osborne of the Grayson Militia. So we know that Enoch Osborne and Daniel Boone served together in a company of only 50 or so men on the Clinch River frontier during Lord Dunmore's War. Click here to see one of the original pay lists of men in the company under Captain Looney and the amount of their pay. Ephraim, Enoch's father, also served under Captain Looney, and his pay is recorded on another list as is Stephen Osborne. (On these lists Osborne is spelled "Osburne.")
Osborne family stories in Grayson County contend that Enoch Osborne fought in the Battle of King's Mountain, and also the Battle of Guilford Courthouse. Many historians have ruled this out based on muster rolls of the companies in those battles. Further examination, however, has found that many muster rolls were incomplete, or totally missing. We may never know for sure if Enoch fought in either of those two historic battles.
MORE INFO HERE: http://www.graysonosbornes.com/13.html