The first white men to enter Madison
County's area were probably professional Indian trader John Findley, Daniel
Boone, and four companions who came into the region in 1769 on a hunting and
exploring expedition. The following year Boone's brother Squire went back to North
Carolina to replenish supplies, leaving Daniel to explore as far as the Falls of
the Ohio at present-day Louisville. In July Squire Boone communicated his return
to Kentucky to Daniel by carving "1770 Squire Boone" on a prominent
rock in the southern section of the area that became Madison County, near a
campsite they had previously made. Now famous, Squire Boone's rock is displayed
today inside the Madison County Courthouse.
In 1774 a group of five adventurers
led by Judge Richard Henderson of North Carolina formed the Transylvania Company
to obtain land west of the Appalachians from the Indians. Henderson successfully
purchased from the Cherokee nearly 20,000,000 acres of land including
present-day Madison County. Daniel Boone was employed by the company in 1775 to
cut a trail into the land through the Cumberland Gap and to establish a
settlement on the south bank of the Kentucky River.
Boone and his crew of thirty men marked a path
that would become known as the Wilderness Trace (later called Road). Originally
only a bridle path that wound through the county's north-south axis, it provided
access to settlers from Virginia and North Carolina via the Cumberland Gap.
Remnants of it still exist in Madison County near U.S. 25 South and Red House
Road, KY 388. When Indians attacked them near the present-day Bluegrass Army
Depot in Madison County, Capt. John Twetty fell mortally wounded. The party
hastily constructed a small, palisaded log enclosure about six feet high to
repulse their attackers. This temporary fortification, called Twetty's Fort
after the man whose burial place lay inside, is considered to have been the
first fort erected in Kentucky.
Pressing on, the men reached the Kentucky
River and built another small fort near the mouth of Otter Creek. When Richard
Henderson arrived in April with about forty settlers, he directed the
construction of a larger fortification nearby. Called Fort Boone, it consisted
of approximately twenty-six single-room, one-story log structures joined by a
stockade wall having two-story blockhouses at each of the four corners. Thus
guarded by the fort, the Wilderness Road became safer for settlers.
In 1775 the Continental Congress, meeting in
Philadelphia, refused to recognize the existence of a Transylvania Colony. The
following year the state of Virginia created Kentucky County, which included the
area now occupied by Madison County, out of portion of a Fincastle County.
Having a town plat of twenty acres divided into 119 lots, streets, and a common
area, in 1779 Boonesborough (originally spelled Boonsborough) became the first
town in Kentucky County to be chartered by Virginia. Kentucky County was divided
into three counties in 1780-- Jefferson, Fayette, and Lincoln--with the area
comprising today's Madison County being a part of Lincoln County.