The Shawnees, having lost the brief Dunmore’s War, had been compelled to cede their claim to Kentucky.

Richard Henderson, a judge from North Carolina, had organized a land speculation company with a number of other prominent North Carolinians on August 27, 1774.

Originally called "Richard Henderson and Company", the name had been changed to the "Louisa Company", and then to the "Transylvania Company" on January 6, 1775.

The men hope to purchase Kentucky land from the Cherokees, who still have a claim to the region, and establish a British proprietary colony.

In Henderson meets with more than twelve hundred Cherokees, including Cherokee leaders such as Attacullaculla, Oconostota, and Dragging Canoe, at Sycamore Shoals (present day Elizabethton in northeastern Tennessee).

In the resultant Treaty of Sycamore Shoals, also known as the Treaty of Watauga, dated March 14, 1775, Henderson purchases all the land lying between the Cumberland River, the Cumberland Mountains, and the Kentucky River, and situated south of the Ohio River.

The land thus delineated, twenty million acres (eighty-one thousand square kilometers), encompasses an area half as large as the present state of Kentucky.

Henderson's purchase is in violation of North Carolina and Virginia law, as well as the Royal Proclamation of 1763, which prohibits private purchase of native land.

Henderson may have believed that a recent British legal opinion (the Camden-Yorke opinion) had made such purchases legal.

Richard Henderson, before negotiating the Sycamore Shoals treaty, had hired Daniel Boone, an experienced hunter who had explored Kentucky, to travel to the Cherokee towns and inform them of the upcoming negotiations.

Boone is afterwards hired to blaze what becomes known as the Wilderness Road, which goes through the Cumberland Gap and into central Kentucky.

Along with a party of about thirty workers, Boone marks a path to the Kentucky River, where he establishes Boonesborough (near present-day Lexington, Kentucky), which is intended to be the capital of Transylvania.

Other settlements, notably Harrodsburg, are also established at this time.

Many of these settlers have come to Kentucky on their own initiative, and do not recognize Transylvania's authority.

After Henderson arrives at Boonesborough, the Transylvania Convention is convened in May.

The colony is organized into a political community, with president, legislature, and judges.

With the outbreak of the American Revolutionary War in 1775, Transylvania seeks recognition from the Continental Congress as a fourteenth colony.

The Congress refuses to recognize the colony since both Virginia and North Carolina claim the land in question.

Kentucky's settlers, as the American Revolutionary War began in the East, had become involved in a dispute about the region's sovereignty.

Richard Henderson, a judge and land speculator from North Carolina, has purchased much of Kentucky from the Cherokee in an illegal treaty.

Henderson intends to create a proprietary colony known as Transylvania, but many Kentucky settlers do not recognize Transylvania's authority over them.

In June 1776, these settlers select George Rogers Clark and John Gabriel Jones to deliver a petition to the Virginia General Assembly, asking Virginia to formally extend its boundaries to include Kentucky.

Clark and Jones travel the Wilderness Road to Williamsburg, where they persuade Governor Patrick Henry to create Kentucky County, Virginia.

Before the Revolution had been a leading land speculator in lands west of the Appalachians where Virginians, including George Washington and Thomas Jefferson, have sought control from Native Americans.

Clark has been given five hundred pounds (two hundred and thirty kilograms) of gunpowder to help defend the settlements and is appointed a major in the Kentucky County militia.

The Revolutionary War intensifies in Kentucky in 1777.

British lieutenant governor Henry Hamilton, from his headquarters at Fort Detroit, arms and encourages his Native American allies to wage war on the Kentucky settlers in hopes of reclaiming the region as their hunting ground.

The Continental Army can spare no men for an invasion in the northwest or for the defense of Kentucky, which is left entirely to the local population.

George Rogers Clark spends several months defending settlements against the Native American raiders as a leader in the Kentucky County militia, while developing his plan for a long-distance strike against the British.

Clark's strategy involves seizing British outposts north of the Ohio River to destroy British influence among its Native American allies.

In December 1777 Clark presents his plan to Virginia's governor, Patrick Henry, and asks for permission to lead a secret expedition to capture the British-held villages at Kaskaskia, Cahokia, and Vincennes in the Illinois country.

Governor Henry commissions Clark as a lieutenant colonel in the Virginia militia and authorizes him to raise troops for the expedition.

George Rogers Clark's volunteers had departed the Falls on June 24 to begin their military campaign.

In July 1778, Clark and about one hundred and seventy-five men cross the Ohio River at Fort Massac and march to Kaskaskia, capturing it on the night of July 4 without firing their weapons.

Lieutenant Colonel Clark and his officers, after heavy recruiting, have attracted volunteers from Pennsylvania, Virginia, and North Carolina.

The men gather in early May near the Falls of the Ohio, south of Fort Pitt.

The group of one hundred and fifty soldiers, eventually known as the Illinois Regiment spends about a month along the Ohio River preparing for its secret mission.

They set out or the Illinois Country on May 12 from Redstone, today's Brownsville, Pennsylvania, taking along eighty civilians who hope to claim fertile farmland and start a new settlement in Kentucky, and ...

Clark and about one hundred and seventy-five men cross the Ohio River at Fort Massac in July 1778, and march to Kaskaskia, capturing it on the night of July 4 without firing their weapons.

Captain Joseph Bowman and his company of men capture Cahokia in a similar fashion on July 5 without firing a shot.

The garrison at Vincennes along the Wabash River surrenders to Clark in August.

Several other villages and British forts will subsequently be captured, after most of the French-speaking and native inhabitants refuse to take up arms on behalf of the British.