the tip of Buchanan County marks the Kentucky-Virginia-West Virginia border
Source: US Geological Survey (USGS), Wharncliffe, WV-VA-KY 7.5-minute topographical quadrangle map (2014)
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.
In 1776, the General Assembly divided Fincastle County to create Washington, Montgomery, and Kentucky counties. The name Fincastle disappeared, since it honored the family of Lord Dunmore at a time when he had fled from the developing American Revolution in Williamsburg.
The straight line of the Virginia-North Carolina boundary and the twisted boundaries of two natural features - the Big Sandy River and the Cumberland Mountains - were used to define the edges of the new county called Kentucky:1
In 1780, Kentucky County was subdivided into Jefferson, Lincoln, and Fayette counties.
Being west of the Allegheny Front was key to the development of Kentucky. Settlers crossed through Cumberland Gap to obtain cheap land, and that land was used for farming. Surplus agricultural products, including deerskins, lumber, and corn converted into whiskey, was floated down the Sandy, Kentucky, and Cumberland rivers to Ohio River and then down the Mississippi River to market at New Orleans.
In contrast, Virginia's leaders living east of the Appalachians remained focused on trade via rivers that connected to the Chesapeake Bay. Georgee Washington feared that the United States would lose support of western settlers unless new transportation infrastructure could bring their products across the mountains to port cities on the Atlantic seaboard. Washington personally supported the Chesapeake and Ohio Canal to facilitate the connection between west and east via the Potomac River.
Virginia's leaders also supported construction of a canal on the James River, drawing trade from the Ohio River to Richmond. Virginia's western lands in the upper Ohio River and Kanawha River watersheds could be connected by roads and canals to Fall Line ports.
Further south, it was a different challenge. A road or canal from the Cumberland Gap to a Virginia port was clearly not feasible. The costs to carry heavy freight by horse-drawn wagon for 350-400 miles to Richmond, including a crossing of the Blue Ridge, were too high for farmers to make a profit. The only feasible option was to float freight down the rivers, and in Kentucky the rivers float west to the Mississippi River.
in the late 1700's, there was no realistic way to construct a canal or road to carry Kentucky's agricultural products through Cumberland Gap to a port on the Atlantic seaboard
Source: ESRI, ArcGIS Online
The General Assembly created additional counties as population increased in the far western corner of the state, but made few investments in the Kentucky country. The legislature was unresponsive to requests to fund roads and canals west of the Allegheny Front that would send agricultural goods down the Mississippi River, rather than to a port in Virginia.
Virginia even gave away its lands north of the Ohio River, ceding the Northwest Territory to the new Continental Congress. Retaining Virginia's claim to the far western lands would have required funding for defense against Native Americans and the British in Canada, and for transportation projects that would not bring trade to Alexandria, Fredericksburg, Richmond, or Petersburg.
Settlers in Kentucky County, on the western side of the Cumberland Mountains, saw few benefits from remaining part of Virginia. Rather than pay taxes to a legislature in Richmond that would not support trade to New Orleans, and might not respond to raids from Shawnee living north of the Ohio River, it made more sense to convert the Kentucky region into an independent state. There was even a possibility it could become part of a new colony/state of Transylvania, proposed by a land speculator who purchased land rights from the Cherokees in the 1775 Treaty of Sycamore Shoals.
There were 10 conventions in Kentucky between 1784-1792, that debated the details and future organization of government. in 1792, the US Congress made Kentucky the second new state to enter the Federal union. Kentucky was a state that supported slavery, and its admission balanced the addition of Vermont in the north.2
after creation of Kentucky, lands north and east of the Big Sandy River and its Tug Fork tributary were still Virginia - until West Virginia was created in 1863
Source: Library of Congress, A new map of the United States. Upon which are delineated its vast works of internal communication, routes across the continent &c. showing also Canada and the Island of Cuba
As part of the deal to support the creation of a new Commonwealth of Kentucky, Virginia reserved lands between the Green and Cumberland rivers for honoring warrants for military service in the French and Indian War. That reservation was in addition to the Virginia Military Reserve north of the Ohio River in the Northwest Territory.
Virginia awarded land bounties to recruit soldiers, and reserved land within Kentucky as well as Ohio for land claims of veterans
Source: Kentucky Secretary of State, Neal Hammon Series of Maps - Virginia's Western Counties, 1780
In 1792, Virginia supported Kentucky's entrance into the Federal union as an independent state, with exterior boundaries unchanged since Kentucky County was formed in 1772.
Before agreeing to the establishment of a new state, Virginia used its claims to the Northwest Territory as a bargaining chip to ensure the state retained control over the Kentucky district.
State officials were concerned that the new national government might declare pre-existing claims void and force people with Virginia-authorized land claims to repurchase their land, since the traditional Virginia pattern of transferring land to private ownership was inefficient and created excessive legal confusion. The promise of a future voluntary cession of lands north of the Ohio River kept the Continental Congress from interfering with Virginia's management of Kentucky south of that river.
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 the middle of the river. That left Virginia in control of traffic on the entire Ohio River, just as Maryland had established title to the entire Potomac River.
When Kentucky became an independent state, it inherited the claim of control to the low water mark on the northern shore of the Ohio River. The General Assembly also determined in the legislation authorizing Kentucky independence that3
Thomas Jefferson suggested that the boundaries of Kentucky should be part of his plan for creating new states out of western lands, starting at the mouth of the Kanawha River. Virginia was the largest state, both in population and acreage, in the new Federal government. Even after the separation of Kentucky, he felt that Virginia would be too large and unable to govern effectively all the territory that it would retain.
all of Kentucky was once a county in Virginia
Source: National Oceanic and Atmospheric Administration (NOAA), National Geophysical Data Center (NGDC)
Jefferson believed that democratically-elected leaders could not effectively manage large geographic areas, that governments dominated by business interests along the Atlantic seaboard would not be sensitive to concerns of farmers located west of the Alleghenies, and that governments would be more representative of the voters' interests if the Northwest Territory was subdivided into small states. His proposal for Kentucky's boundaries was intended less to benefit the new state and more to improve government in Virginia's remaining western lands.4
Thomas Jefferson proposed shrinking the size of Virginia, dividing Kentucky in half, and creating many small states out of the western lands acquired in 1783
Source: Manifest Destiny - Shaping America's Culture and Borders
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.
northern tip of VA-KY survey line (note that Virginia retained rights to the far shore of the Tug Fork, and West Virginia inherited those rights to the entire river)
Source: USGS, Digital Raster Graphic (DRG) of Wharncliffe 7.5 minute topo quad, downloaded from GIS Spatial Data Server at Radford University
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 Russell Fork. At the current location of Breaks Interstate Park there is a clear gash in Pine Mountain there, cut by the Russell Fork - a tributary of Levisa Fork, which is a tributary of the Big Sandy River, which runs into the Ohio River near Ashland, Kentucky.
the Russell Fork cuts through Pine Mountain at Breaks Interstate Park
the Pound Fork flows into the Russell Fork before flowing across the Kentucky-Virginia border like the Levisa (Louisa) Fork, while the Tug Fork defines the Kentucky-West Virginia and Kentucky-Virginia borders
Source: Library of Congress, Colton's map of the southern states (1861)
At the Russell Fork, the surveyors quit trying to follow natural features. Instead of zig-zagging across the rugged landscape to define the watershed boundary, they marked a 45-degree line straight line northeast to Tug Fork, another tributary of the Big Sandy River.5
at the Russell Fork, the VA-KY line stops tracing the watershed boundary and becomes a straight line to Tug Fork
Source: USGS, Digital Raster Graphic (DRG) of Elkhorn City KY-VA 7.5 minute topo quad,
downloaded from Kentucky Geological Survey
In 1776, the Virginia General Assembly defined the "main or north easterly branch" of the Tug Fork as the Kentucky County line. When it came time to determine which stream qualified as the "main or north easterly branch" to serve as the boundary between the states of Kentucky and Virginia, the surveyors and their commissioners made a judgment call.
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. Discussions that evening 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.
The starting point of the Big Sandy River, the confluence of the Levisa Fork and Tug Fork, is now the location of Louisa (Kentucky) and Fort Gay (West Virginia). The 1799 meeting of commissioners determined the Virginia-Kentucky boundary met in 1799,
That night a major rainstorm caused the Levisa Fork to rise, and in the morning it rather than the Tug Fork appeared to be "main or north easterly branch." Despite the physical change, 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.6
the yellow on the map shows how much of Kentucky would have been placed in Virginia (now West Virginia) if the Levisa Fork had been chosen as the "main or north easterly branch" of the Big Sandy River
Source: ESRI, ArcGIS Online
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)
after the Civil War, Virginia added Dickinson County on its side of the Virginia-Kentucky border (as defined by the Cumberland Mountains)
Source: Library of Congress, Lloyd's map of the southern states showing all the railroads, their stations & distances, also the counties, towns, villages, harbors, rivers, and forts.