William Winchester arrived in 1729 in Baltimore,MD and some of his descendants went west, particularly Gen. James Winchester, an early settler of Tennessee.
In the mid 1700’s Willoughby Winchester was among the first settlers of the Craven (Ninety Six District) of SC upcountry and one or more Thomas Winchester is found in deeds and court records of Lunenburg & Halifax Co, Virginia as well as Orange Co, NC.
In the late 1700's John Winchester is listed in the 1768 NC Rowan Co Tax list among the Haw River settlement (now Guilford/Rockingham Co, NC). A William and Thomas Winchester are listed in the 1766 Mecklenburg Co, NC Militia. William and Daniel are listed in the Revolutionary War NC Militia of Mecklenburg, NC (later Union Co). Francis Winchester and several sons are listed in 1800 and later Burke Co, NC census. There is no documentation that connects the Guilford, Mecklenburg or Burke Winchester families together.
Winchesters are documented by the mid 1800’s settlements of New Brunswick and Nova Scotia, Canada. Some of these arrive from England and some from New England.
The connection of these Winchester groups with one another is unproven. We are fairly certain these three North Carolina groups did not come from Kent Island, MD, but possibly came from New England via Philadelphia or close-by ports. English, German, Scottish, Irish settlers used the Great Wagon Road in the1760’s through Virginia’s Shenandoah Valley to settle the Piedmont areas of North and South Carolina. Beginning in the early 1800’s all these eastern seaboard Winchester families supplied several generations of migrations into the deep south and westward across the Appalachian Mountains into western NC, Georgia, Tennessee, Kentucky, Texas and the Plains states.
source: Winchester Family DNA Project - Background