The claim of Virginia to the western lands, including Kentucky, is based on the Second Charter from James II, issued in 1609. It defined Virginia as extending from sea to sea, west and northwest. As European settlers migrated west, the Virginia General Assembly created new counties with local courthouses where surveys and land deeds were recorded. The boundaries of Kentucky were defined first in 1772, when Kentucky County was created out of Fincastle County.
In 1792, the Virginia-Kentucky boundary became a state boundary when Kentucky entered the Union as the 15th state. The Virginia-Kentucky state boundary involved less conflict and less debate than the other boundaries that now exist between Virginia and North Carolina, Tennessee, Maryland, and the District of Columbia.
Kentucky was first occupied by humans roughly 15,000 years ago. When the Virginia colonists began to carve out farms west of the Blue Ridge, the Appalachian Plateau was used primarily by Cherokee and Shawnee tribes.
The Iroquois also traveled south through the region from New York, typically on short-term raids against the Cherokee and other Native American groups. In negotiations to redefine the western edge of legitimate colonial settlement after King George III issued the Proclamation of 1763, the Iroquois sought compensation before relinquishing their rights to the land south of the Ohio River and west to the Tennessee River.
That Iroquois claim was based on the right of conquest over the Shawnee. Though that claim was highly questionable, in the 1768 Treaty of Fort Stanwix the British paid the Iroquois to extinguish whatever rights the Iroquois possessed. When the Cherokee relinquished their claim to Kentucky in the 1775 Treaty of Sycamore Shoals, they warned Richard Henderson and his Transylvania Company that they were purchasing a "a dark and bloody ground" with conflicts still remaining over ownership.
Colonial exploration into far western Virginia was triggered by land speculators. They obtained large land grants from the king, then sought to survey and sell parcels to the growing population in the colonies. The gentry of Virginia and Pennsylvania coerced their colonial governments and Native Americans into making land speculation "legal," then sponsored expeditions to explore, hype, and sell western lands.
In 1749, the Loyal Land Company obtained a grant from the Governor's Council to 800,000 acres on the Appalachian Plateau, including much of what would become Kentucky. That land speculation syndicate was composed of members of the gentry who enough substantial clout in Williamsburg to get the governor's authorization for "free land." The Greenbrier Company had set the example in 1745, when it obtained a grant for 100,000 acres in the Greebrier Valley of modern-day West Virginia.
The Ohio Company also obtained a different land grant in 1749. The Ohio Company authorization was for 500,000 acres, with 300,000 acres contingent upon settling 100 families within seven years). The Ohio Company grant was for lands near the forks of the Ohio River, further north from the lands desired by the Loyal Land Company. The leaders of the Loyal Land Company were concentrated in the Piedmont, while the gentry in the Ohio Company were largely from the Northern Neck.
The first colonial explorers into the Appalachian Plateau left little indication of their presence. The first documentation of a crossing through the Cumberland Gap was the 1750 journal of Dr. Thomas Walker, a key member of the Loyal Land Company.
Walker was exploring across the mountains to determine what areas to advertise, survey and sell. The grant to the Loyal Land Company came at no cost, but required lands to be surveyed within four years. The syndicate would gain revenue only if settlers purchased individual parcels. Walker also was identifying possible routes that would be used to cross the mountains, which is why he examined Cumberland Gap.
The Ohio Company efforts to build a fort at the headwaters of the Ohio River were blocked when French troops moved into the area, seized the "Forks of the Ohio," and constructed Fort Duquesne (later the site of Pittsburgh). The Virginia response led by George Washington triggered the French and Indian War. Tense fighting with Native American tribes during that war delayed colonial efforts to occupy lands west of the Atlantic Ocean-Gulf of Mexico watershed divide.
In 1763, the Treaty of Paris that ended the French and Indian War also defined the Mississippi River to be far western edge of Virginia. The colony no longer stretched from "from sea to sea" because, in that treaty, the English accepted the Spanish claim to lands west of the Mississippi River.
Until 1770, just one county (Augusta) included all the land claimed by Virginia that was west of the Blue Ridge. the western edge of Augusta County extended south of the Fairfax Grant, between the North Carolina border and the Great Lakes, all the way west to the Mississippi River. In 1770, Botetourt County was carved out of Augusta, and in 1772 Fincastle County was created out of Botetourt.
Fincastle County was still huge. Boundaries were defined by a line that ran from the Ohio River up the New River to "Culbertson's creek" (perhaps the mouth of the Greenbrier River in West Virginia), then east across Giles County to roughly I-81 (near Exit 118 to Virginia Tech...), then west of Radford though Floyd County to the crest of the Blue Ridge, on south to the North Carolina border, and then west to the Mississippi River.1
British leaders struggling to pay for the recent war thought it was time to rein in the Virginians, and minimize the costs of expansion. So in 1763, officials in London determined that English settlement should be restricted to the Atlantic Ocean watersheds, and King George III issued the Proclamation of 1763 banning settlement west of the Appalachians.
This ban (and the concurrent opening of the Natchez territory in Mississippi to settlement) was expected to minimize disputes over territory with the Iroquois, Shawnee, Cherokee, and other tribes. Fewer disputes would, at least in theory, minimize the military costs for protecting English settlements.
In Williamsburg, there was a different perspective. Lord Dunmore, though the royal governor of Virginia, was more than willing to ignore the restrictions in the Proclamation of 1763, the 1768 Treaty of Fort Stanwix, and the 1774 transfer of Virginia's western lands to the province of Quebec.
In 1773, Dunmore overruled objections from local - Fincastle County - officials and approved private surveys for land claims at the obviously-valuable but far-away Falls of the Ohio River (now Louisville). He also declared that military warrants, which entitled officers and soldiers who fought in the French and Indian War to land grants, could be filed anywhere in Virginia. In addition to helping make Kentucky more attractive by facilitating land claims, Dunmore even initiated war with the Shawnee and forced them to withdraw from territory south of the Ohio River.2
In 1775, Lord Dunmore was forced to flee Williamsburg as the colony joined what became the American Revolution. Virginia officials faced the same choices as the British officials: how much should be invested in protecting the scattered settlements on the frontiers?
The "rebels" in Williamsburg were reluctant to supply arms and ammunition to the frontier settlers west of Cumberland Gap, when George Rogers Clark arrived in Williamsburg and requested supplies. However, after he complained "if a country were not worth protecting, it was not worth claiming," the rebel governor (Patrick Henry) quickly provided the requested lead and powder.3
In 1776, the General Assembly separated Kentucky County from the lands east of the Cumberland Mountains, and used the Big Sandy River to define the new county boundaries as:4
In 1780, Kentucky County was subdivided into Jefferson, Lincoln, and Fayette counties.
Settlers on the western side of the Cumberland Mountains had little interest in paying taxes to a legislature in Richmond. The General Assembly was dominated by Chesapeake Bay-oriented gentry, and was unresponsive to concerns regarding navigation on the Ohio/Mississippi rivers (the primary outlet for shipping goods from Kentucky to market).
Legal appeals from local court decisions required traveling to Richmond. Plans for funding local militia defense - or attacks on Native Americans across the Ohio River - required approval from so far away, it was unlikely Virginia could protect its distant frontier. The General Assembly created additional counties as population increased in the far western corner of the state, but made no investments in the Kentucky country.
It was obvious that Virginia would provide almost no services to the southwestern edge of the state, and that Kentucky would become an independent political unit. There was even a possibility it could become part of a new colony of Transylvania, proposed by a land speculator who purchased the rights of the Cherokees. There were 10 conventions in Kentucky between 1784-1792, when the US Congress made Kentucky the second new state to enter the Federal union to balance the addition of Vermont in the north.5
As part of the deal, Virginia reserved lands between the Green and Cumberland rivers for honoring warrants for military service in the French and Indian War - comparable to the Virginia Military Reserve north of the Ohio River in what became the Northwest Territory, after Virginia ceded that land to the new Federal government.
Virginia awarded land bounties to recruit soldiers, and designated land within Kentucky for award of that land
Source: Kentucky Secretary of State, Neal Hammon Series of Maps - Virginia's Western Counties, 1780
Virginia was slow in establishing Kentucky as an independent state in part because Virginia's claims to the Northwest Territory were a bargaining chip to solidify Virginia's control over Kentucky. The traditional Virginia pattern of transferring land to private ownership was inefficient and created excessive legal confusion, but state officials were not willing to risk that the new national government might declare all existing claims void and force everyone to repurchase their land.
In the cession of the Northwest Territory Virginia carefully defined its boundary as the low water mark on the northern shore of the Ohio River (not to the middle of the river), thus claiming the entire Ohio River - just as Maryland had established title to the entire Potomac River.
The General Assembly determined, in the legislation authorizing Kentucky independence, that6
Thomas Jefferson proposed that Kentucky should be enlarged, not so much for Kentucky's benefit as for Virginia's. Jefferson had proposed the Northwest Territory be subdivided into small states, and felt that Virginia was unable to govern effectively all the territory it would retain after the separation of Kentucky. From Jefferson's perspective, Kentucky should have included all the territory southwest of the confluence of the Kanawha River and the Ohio River.7
To mark the boundary in 1799, Kentucky and Virginia followed the time-honored process used for defining Virginia's boundaries: each state appointed commissioners and surveyors. At the time, all the land on the northeastern side of the Big Sandy/Tug Fork rivers was still Virginia; West Virginia was not created until 1863.
They followed the Big Sandy/Tug Fork upstream to a point they defined as the intersection of the crest of Cumberland Mountain. They also surveyed northeast along the crest of Cumberland Mountain, starting from "seven pines and two black oaks" on the Walker Line (which was Virginia's definition of its border with Tennessee, in 1799).
The commissioners and surveyors traced the mountain ridge northeastward. They cut away from the Cumberland River/Powell River watershed divide (the Tennessee Valley Divide) and moved to the crest of Pine Mountain, southwest of the current Pound, Virginia. The commissioners and surveyors followed the ridge of Pine Mountain to the current location of Breaks Interstate Park, where Russell Fork (a tributary of Levisa Fork, which is a tributary of the Big Sandy River, which runs into the Ohio River...) cuts through the mountain. There, the surveyors quit following the natural features and marked a 45-degree line straight line northeast to Tug Fork.8
Virginia originally drew the Fincastle county line at the Tug Fork, but determining the "main or north easterly branch" required some judgment. According to one report, the commissioners and surveyors met at the confluence of the Tug and Levisa forks of the Big Sandy River on October 13, 1799. Their discussions were mellowed by strong drink, and they agreed that the Tug Fork was the larger tributary and thus the "main Branch."
The officials of each state planned to sign documents to that effect the next morning. In the evening a major rainstorm caused the Levisa Fork to rise - but on October 14, the "true Kentuckians and Virginians agreed to ratify while sober, what they had agreed while drunk" and the Tug Fork was defined as the boundary line.9
shape of Virginia after 1790 (when Kentucky became an independent state) until 1863 (when West Virginia was created)
Source: Library of Congress, New map of Virginia (1861)