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Speculators and Explorers
Push further into Shawnee and Cherokee Territory


By the late 1760's Kentucky began to replace Virginia, North Carolina and South Carolina as the new frontier. The Revolution drew near. Settlement on Indian lands was illegal under British rule. Americans continued pushing west over the mountains anyway.

The Cherokee Warrior Path

The Cherokee Warrior Path was a secret passage to the Kentucky River and the "Blue Grass" country. It passed through the mountains at a place called "Indian Gap." Daniel Boone was determined to find that gap.

He went exploring with William Bryan and his brothers, the sons of Morgan Bryan. (See Virginia-Carolina). Meanwhile Richard Henderson embraced grand land speculation dreams. He meant to create a whole new 14th colony across the mountains. He was happy to finance Boone's search for the elusive passage now referred to as the "Cumberland Gap." (See Virginia-Carolina)

After many failed attempts, Boone's party, following a hunter's trail through the Powell Valley one day in June 1769, came upon the legendary path. They climbed through the Gap and followed the path another fifty miles along the west fork of the Rockcastle River and mounted the highest knob they could find to assess their discovery. They were not disappointed for they saw spread out before them the meandering Kentucky River and the rolling ridges extending forever into the western horizon. They had found the gateway to the new frontier. See reference (1).

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First Boone-Bryan settlement in Kentucky

After his discovery Daniel remained in Kentucky the rest of the year, much of it all alone. When he returned to his family on the Yadkin River (North Carolina) he recruited five families to return to Kentucky with him. Among the families were the Bryans--his wife Rebecca Bryan's family. Daniel led them through the Gap and into the Kentucky River region. About October, he sent his son James and several other of the young men back to North Carolina for supplies but the young men were ambushed and James was killed. When word reached the expedition, Daniel and the Bryans, grief stricken, turned back.

Others in the Boone-Bryan expedition continued to press further into Indian Territory. It was extremely hazardous because the Colonial government refused to defend such adventures.It was busy growing general dissent.

Boone and William Bryan headed out for the wilderness once again that same year and explored the North Fork of the Elkhorn River in Kentucky and established a village they named "Boonesborough."

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In 1774 James Harrod led a team of 30-50 men deep into Kentucky and founded the town of Harrodsburgh near the Kentucky River. They platted town and garden lots, built a cabin and then retreated under threat from the Shawnee.


At this time trouble was seething on many fronts. Lord Dunsmore, Governor of Virginia, was determined to take Kentucky for Virginia and mounted a war to accomplish it.( Colonial Pennsylvania web pages)

A Map entitled Dunmore's War, 1774, shows notes by surveyor Floyd. See reference (2) It states: "found Harrodsburg destroyed July 14, 1774." Two other notes bear mention:

"Surveyed 400-500 acres at Scioto and Ohio May 1, 1774 for Patrick Henry"
"Surveyed 1000 acres on Elkhorn April 16, 1774 for George Washington"

George Rogers Clark led a group of Pennsylvanian back to restart the settlement in 1775.

NOTE: The names of some Harrodsburgh settlers can be determined from writings left by members of the expedition. "Mercer County Online" has posted these writings. As of 4-13-09 try this link: Harrodsburg Settlers

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Obviously the market for frontier land was booming. Richard Henderson seized the opportunity to promote his fourteenth colony. ("../colovirg.html#hend") (See Colonial Virginia) By this time he had a license to practise law, had been appointed to the Superior Court and had wealth and influence. He formed the "Transylvania Company". He convinced Daniel Boone to go with him to the Watauga River to meet with the Cherokee.

Daniel and Richard met with the tribal leaders at Sycamore Shoals in 1775 and negotiated the purchase of extensive Cherokee land in Kentucky. Henderson offered the land for sale at twenty shillings per hundred acres and hired Boone to blaze a wagon road through the Cumberland Gap all the way to "Boonesborough."

Daniel, famous for his survival skills, not his business acumen, agreed to supervise the work of 31 axe men and to hack out the treacherous route through the rugged mountains for thirty three cents a day. He had to buy his powder from Henderson. Apparently Daniel did not do the math--he ended up working eight days for each pound of powder. Bad weather, dense forest, and Indian attacks hampered completion.The road was notoriously rough. Construction of the fort at Boonesborough began immediately.

The first contingent of settlers left with Daniel Boone and his family that very year. Among them were the Hendersons: Richard, his brother Nathaniel and Nathaniel's son Samuel. They built the village of Boonesborough and attempted against great odds to reside there.

Henderson was determined that the colony's government would be by popular representation. The first order of business was to order elections throughout the Kentucky settlements. On May 8, 1775 he convened the first legislative assembly with representatives from Boonesborough and three other settlements.

But Judge Henderson' scheme was in defiance of the Virginia colonial government's stated policy with respec to wild lands. Considering the Governor's recent war to claim Kentucky, the policy seems rather inconsistent. The Virginia provincial government declared Henderson's sales illegal. The government then offered the very same land free in 400-acre parcels to anyone who would improve it and raise corn on it before 1778.

The names of original Boonesborough settlers are listed online with dates, comments and sources. The posting is provided by Don Chesnut. The URL has changed over time, but it is easy to find using your favorite search engine with the keywords Fort Boonesborough and settlers.At present try this one: Early Settlers

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Bryan's/Bryant's Station

In 1776 William Bryan led a party to explore the Tennesse. He then founded a settlement 16 miles from Boonesborough and called it Bryan's Station.In the spring he had the land cleared and planted and then built a cabin. Just about that time the British began enticing the Shawnee to chase settlers out of Kentucky. The raids became so severe that by the time William returned to North Carolina to collect his family, going to Kentucky was out of the question. The Bryan family was divided over the war with England. Many families in western North Carolina sided with the King. They were called Tories or Loyalists. Wealthy tidewater Whigs (now Patriots) had always held the power in North Carolina and the western people mistrusted them. William's brother, Samuel Bryan, joined the Loyalist Militia. By 1777 the Whigs had control of the Yadkin area. The Boones and Bryans were labelled Tories. While Samuel went into hiding the other Boones and Bryans took oaths of loyalty to the Patriot cause--all except William Bryan. William was apparently ambivalent. He sidestepped the issue by removing to Kentucky.

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Attacks on the Kentucky Forts

Many settlers--some Tories--pushed beyond the previously agreed-upon limits crossingthe Great Smokies and Alleghenies into Kentucky and the Ohio Valley. This outraged the tribal leaders who went on the war path all along the frontier. Although the new "United States" maintained a protective garrison at Fort Pitt in Western Pennsylvania, the frontier was vulnerable to attack by the British who controlled Lake Erie from its headquarters at Detroit. The British command manipulated the Ohio tribes into defending the Ohio country by terrorizing the frontier settlements and thereby preventing further intrusion into the territory. Only three settlements had survived in Kentucky by 1777. One of these was Daniel Boone's settlement. When it was assaulated in 1777 by Shawnee, Daniel sent word to the Bryans for help.William Bryan's son and George Boone went to aid in the defense of Boonesborough.

In 1778 Daniel Boone was captured by the Shawnee and taken to their village at Chillicothe on the Scioto River. On the long journey north Daniel ingratiated himself to the chief and won his confidence by adopting their dress and shaving his head. While in captivity he learned that the Shawnee planned to attack Fort Boonesborough. He slipped out of the village one night and made his way back over the 160 miles to Boonesborough to warn his people. He sent for George Rogers Clarke to aid in the fort's defense.

On September 7, 1778 400 Shawnee and twelve French partisans came to the Fort and demanded surrender. Always choosing deception over combat, the settlers asked for time to think it over. They held out inside for several days but eventually the Shawnee began to lob torches into the fort. The settlers defended their fort for thirteen days. The Shawnee and partisans retreated.

Life was too hazardous so Daniel's wife Rebecca Bryan Boone and the children reluctanly returned to the Yadkin in North Carolina. The Boones and Bryans were in jeopardy in either place. By then Clarke had taken Kaskaskia from the British and renewed interest in frontier settlement had spread across western Carolina and Virginia. But it was clear by 1779 that the Bryans could no longer survive at the Yadkin so William took his son to Bryan's Station and fortified his cabin with a stockade. The Boone and Bryan families made their final move to Boonesborough and Bryan's Station to flee from persecution in North Carolina.

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Elisha Walden

Elisha Walden led an expedition to Kentucky composed of 450 angry "Southside" settlers from Pittsylvania County, Virginia. (See Virginia-Carolina) These folks had been duped in a land scam in the Granville Grants of northwestern North Carolina. Faced with quitrents, fees and fines, they made a mass exodus to the frontier to find more land. (See reference (3)

In 1779 the caravan took Daniel Boone's Wilderness Road to Kentucky. The wagons were strung out over a half mile and quite vulnerable to attack. It plodded along all the way to Bryan's Station. The winter of 1879-80 was severe. The precarious group succumbed to sickness and the livestock died. Game was scarce and their quarters were cramped, unsanitary and susceptible to attack. To make matters worse the Public Lands Commission while making a patrol discovered them and declared them to be illegally occuping property sold to Virginia land speculators. On top of that the Shawnee claimed that three hundred Kentucky militia had raided their village. They retaliated by raiding Bryan's Station. Among those killed was sixteen-year-old William Bryan Jr. Several weeks later in May 1780, William Bryan Sr.'s hunting party was ambushed and William himself was killed.

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Simon Girty

Simon Girty was one of the most hated men at the frontier. He had defected to the enemy in the Revolution. He was the bane of the western settlements.In 1782 he led 400 Indians fronm Chillicothe on the Scioto to attack Bryan's Station. The settlement had grown to forty cabins.

Bryan villagers were wary of frontier tactics and always watchful. They had fortified the settlement and kept constant lookout.When Commandant John Craig saw strangers approach he carried out an improptu diversion. Noting the lack of adequate water within the fortress, he selected twelve women and sixxteen children to carry out a hazardous deception. Among them were Mary and Philadelphia Ficklin the wife and child of Thomas Ficklin. Craig carefully explained the deception and instructed them how to carry it out. The b rave women and children left the fort in plain view of the intruders and headed for the spring, acting as if they were going about their daily routine. Meanwhile Craig sent two riders over to Boonesborough fifteen miles away. The women and children returned safely. Craig then assigned them to battle stations. Once everyone was in position with rifles aimed through tiny slit opening in the wall, Craig commenced his s econd ruse. He sent out a small force to make a show of chasing off the strangers. This face was sufficient to flush the natives fsrom the forest. Thinking they were catching the settlers off guard they attempted to scale the walls, at which point Craig gave orders to the settlers within the walls, including women and children, to open fire, which they did from their assigned positions. Although the battle continued steadily all day long, the fort was spared the destruction that would have followed a surprise attack. See reference (4)

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Boonesborough was attacked again by the Chillicothe tribes in 1782. Daniel Boone lost another son at the Battle of Blue Lics and refused to accept defeat. He led one final furious attack on the Chillicothe village and destroyed it forever.

Lists of the Kentucky militia and the women of Bryan's Station have been posted at the Scott County page at Rootsweb. Another is posted at Fayette County, Kentucky history at Rootsweb. Use the keywords Bryan's Station or Bryan's Station with your favorite search engine. As of 4-13-09 try this : Bryants Station"

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Cumberland Compact

In the spring of 1780 despite the hazards of life at the frontier, Judge Richard Henderson initiated the Cumberland Compact and obtained the signatures of 236 would-be settlers to the land south of Kentucky called "Tennessee." Many of his own family were among the pioneer settlers to Tennessee. Three of his six brothers left Carolina to settle with him at the frontier.

NOTE: The complete list of names of signers of the Cumberland Compact is post at several sites on the Web: images of the document, PDF file, and a viewable list of names at "Founding Families in Nashville TN 1779-80." As of 4-13-09 try this link: Cumberland Compact

Henderson selected Col. John Donelson of Pittsylvania County to conduct a flotilla of settlers to Tennessee. Donelson signed up 160 neighbors. The flotilla of flatbed rafts was headed by Donelson's boat the "Adventure." The voyage covered 985 miles and was plagued by Indian ambush, illness, freezing cold and hunger. Some of the party made it to the Cumberland including the Colonel's daughter, Rachel.See ref 3l.[See note about Rachel ]

Donelson then removed to Kentucky. His received bounty land in the Virginia Military District, for service in the Revolution. Among other survivors of the flotilla trip was John Morton who established Mortonsville. It quickly became the center of trade on the river. Shortly the grain grown by the new farmers in Kentucky roduced a surplus. Whiskey making became the product of choice in Kentucky.

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1 "Fort Boonesborough State Park," Kentucky Department of Parks and Recreation, 1992.

2 Map of unknown origin from Southwestern Pennsylvania Genealogical Society, drawn under the supervision of Louise Phelps Kellogg, no date.

3. Harriet Simpson Arnow, Seedtime on the Cumberland, New York: The MacMillan Co., 1960.

4. Walter Homan Ficklin, The Ficklin Family in America, Denver: 1912.

5. Thomas D. Clark, The Kentucky, New York: Rhinehart, 1942.

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Rachel Donelson:

A great scandal arose over Rachel. Her first husband divorced her. Some said he disowned her, because she disgraced him. She then married a man named Andrew Jackson and went on to become first lady of the new nation. The first husband claimed never to have divorced her in the first place, nullifying her marriage to the President.



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