The sources of the New River are found in the highlands of modern-day Grayson County, Virginia and Ashe County, North Carolina. In the early days of settlement, however, Grayson County was a part first of Augusta County, then (beginning in 1777) of Montgomery County, and (from 1790-1793) Wythe County,Virginia. Ashe County was a part of Rowan and then (from 1777 until 1799) Wilkes County, North Carolina.
Dozens of creeks and smaller streams drain the western slopes of the Blue Ridge and combine to form the New, which then flows generally in a northerly direction from the far northwestern area of North Carolina through Virginia and into West Virginia, where it eventually merges with other streams to become the Kanawha.
The terrain of the headwaters of the New is generally very rugged — high ridgelines separated by narrow valleys. From the piedmont region and foothills of North Carolina, settlements had been extended as far as the Three Forks of the Yadkin River by the 1750s. Once the Seven Years’ (French and Indian) War ended in 1763, a flood of immigrants travelled southward through the Great Valley from Pennsylvania and Maryland, through Virginia — crossing to the east side of the Blue Ridge near present-day Roanoke — and almost due south through Martinsburg (VA) to the vicinity of Winston-Salem, bypassing the more rugged mountain sections of Ashe and Grayson counties.
Because the Great Wagon Road avoided the uplands of Grayson and Ashe, this region became, in essence, a “cul-de-sac” insulated from settlement pressures. It remained for a time the province of the “long hunters”.
Even as Yadkin residents began to feel the pressure of in-migration in the periods just prior to and subsequent to the Revolutionary War, those who desired to resettle further west avoided travel through the New River headwaters. Those who wished to join early settlers on the Clinch and Holston Rivers in far western Virginia, or to follow Boone into Kentucky, would travel back north as far as Wytheville and then down the Wilderness Road toward Cumberland Gap. Others who desired to head west into the Tennessee territories generally would use the Catawba trails to cross over to the Watauga and Nolichucky rivers.
Nonetheless, a few extended families did venture into the more remote fastness of the upper New River.
The earliest attempt at settlement was made by a North Carolinian, Andrew Baker. He first entered present-day Ashe as early as 1753; however, with the onset of Indian hostilities related to the French and Indian War, he returned to the Yadkin settlements until peace was established in 1763. Shortly thereafter, he and other family members settled in the southeastern portion of Ashe. By 1780, despite the Revolutionary War Ashe had several dozen families, including the Pennington, Ray, Roark, Couch, Sturgill and Purkins (Perkins) families.
Also accompanying Andrew Baker and his colleagues were members of the extended — and intermarried — Osborn[e], Hash[e], and Cox families. This group, however, settled on the Virginia side of the border, in present-day Grayson County. They were followed shortly thereafter by Phippses and Howells, Andersons and Bonhams. They were joined by a Swiss-German pietist carpenter, Heinrich Gröb (Grubb), who, like Andrew Baker, had first attempted to settle there prior to the French and Indian War. He was a founder of Grubb’s Chapel Baptist Church.
Historian Paula Hathaway Anderson-Green has provided, in the article cited below, a very good recap of the marital ties among the Osbornes and other families. She also traces their origins back to the Pennsylvania-New Jersey environs surrounding Philadelphia, from whence they migrated down the Great Wagon Road. In future articles dealing with specific surnames, I shall recount some of those details. In the meantime, readers are advised to seek access to the online JSTOR academic journal source as cited below.
 The best history of the Three Forks of Yadkin can be found in Robert W. Ramsey, Carolina Cradle: Settlement of the Northwest Carolina Frontier, 1747-1762, (Chapel Hill: University of North Carolina Press; 1964). It contains extensive indices of surnames, places of origin, and means of immigration of the earliest settlers of the Yadkin region.
 See “Mapping the Great Wagon Road”, by David Walbert, an internet resource on Learn NC, a program of the University of North Carolina at Chapel Hill (http://www.learnnc.org/lp/editions/nchist-colonial/2038).
 Bennett, William D., “Early Settlement Along the New River (NC and VA) Basin” (http://www.nps.gov/history/history/online_books/symposia/newriver-84/sec3.htm), in Proceedings: New River Symposium 1984. Center for Continuing Education, Appalachian State University, Boone, NC.
 Paula Hathaway Anderson-Green, “The New River Frontier Settlement on the Virginia-North Carolina Border 1760-1820”, in The Virginia Magazine of History and Biography, Vol. 86, No. 4, (Oct 1978), pp. 413-431. Available online for many public library patrons at http://www.jstor.org/stable/4248254.