Statehood roots for Highlands House

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By Brad Bowman

The house in Henry County historically known as the Highlands in the rolling hillside just south of Floyd’s Fork and KY 22 was once home to a family whose lives intertwined with Kentucky’s birth as a state and the bloody hunting ground.


The story of the Highlands house cannot separate itself from Kentucky’s beginnings. History tends to favor certain names with fame and legend and coldly forgets others. Daniel Boone’s name embodies the thread of any yarn concerning Kentucky’s early settlers and pioneers. The Callaway family of Henry County lost and fought beside Boone. Their contributions have been forgotten.

Col. Richard Callaway, one of the trailblazers who accompanied Boone on his adventures Kentucky, played a monumental role in defending Boonesborough since its first construction as a settlement. The rescue of Callaway’s daughters and Boone’s daughter Jemima from Shawnee warriors later would inspire James Fenimore Cooper’s rescue scene in The Last of the Mohicans.

Callaway Family

Col. Richard Callaway’s family who lived in Henry County are direct descendants of an indentured servant who came from England to Virginia in 1687. Callaway inherited a substantial amount of land with his brother after his parents reportedly died “of the fever.”

Callaway rose in rank to colonel during the French and Indian War in the Virginia militia. According to family records, Callaway sold off thousands of acres to pay for debt accrued during this time. Callaway later sold 700 more acres and his home in Bedford County, Virginia. During his distress with debt, he met Col. Richard Henderson of North Carolina who founded the Transylvania Company.

The company was formed for land speculation and Henderson planned to sell the land he bought from Cherokee to settlers wishing to migrate west into Tennessee and Kentucky. Henderson hired Daniel Boone as a guide with extensive knowledge of the area and Callaway, who had experience with surveying, was hired to help Boone make a road on what Native Americans called Buffalo Trace — part of the famed Wilderness Trail through the Cumberland Gap.

Callaway built a cabin for his wife and family along the Kentucky River once he and Boone established Boonesborough Fort, as it was originally spelled, on the Kentucky River. Callaway sent for his wife and children. Native Americans would later kidnap three of Callaway’s children and one of those, John ‘Jack’ Callaway, would build the Highlands.


Keziah Callaway wanted to join her older sisters Elizabeth and Frances ‘Fanny’ with Daniel Boone’s daughter Jemima as they went in a canoe to play on the opposite riverbank outside of Boonesborough Fort known as The Hills of Clark. Kezia Callaway, 8, cried according to her account as the older girls refused to let her in the canoe. It was just 10 days after the Declaration of Independence was signed when a party of Cherokee and Shawnee kidnapped the three children. The girls ripped pieces from their dress and aprons leaving them along the trail as the party took them north toward Shawnee Territory.
Callaway and Boone organized a rescue party and followed the torn bits of clothing and the twigs the girls broke along the trail. The children were rescued the next day.


The Shawnee attacked Boonesborough Fort with a force of 350 warriors two years later. In Callaway’s historical account, Boone favored surrendering the fort, but Callaway refused. After 12 days, the Shawnee abandoned the siege and left to hunt for the winter season.

During Callaway’s lifetime, the United States government did not honor the Transylvania Company’s claims. The company, however, was given several thousand acres in Kentucky and Tennessee for their endeavors of colonizing the ‘west.’ One of those land grants encompassed 640 acres awarded to Callaway’s son John.

In 1779, Richard Callaway was elected to the House of Burgesses in Williamsburg, Va. He secured official status for Boonesborough as a settlement with permission to operate a ferry service that would bring settlers across the Kentucky River into the settlement.

The ferry service would be his undoing.

One year later on March 8, 1780, Shawnee attacked Callaway and several workers while they labored on the ferry. Two different accounts report the Shawnee scalped Callaway and paraded his long grey ponytail on a stick. His wife, Elizabeth Callaway, moved to Richmond, Ky. in 1782.

Neither she nor her children could escape the conflict between the settlers and the Shawnee.

Future owner and builder of the Highlands house, John Callaway, played with cousin Jones Hoy in a watermelon patch. A group of Shawnee kidnapped the boys and took them into the Shawnee territory of present day Chillicothe, Ohio.

As with many historical accounts, facts and names differ. All sources credit a French woman, also a captive with her son, for taking care of the two children. An account dictated to her grandson, Allen P. Caperton, names the woman as Magaret Pawley. In another account from an interview with Richard French, a relative of John ‘Jack’ Callaway’s, French said Jack called the woman Peggy Polly.

The Caperton account also states the Shawnee’s chief’s name is White Bark in an account by an Eleanor Widdice, cousin to Mary Clyde Callaway Hardin, wrote in her research that the chief’s name was White Cloud.

Both accounts agree that the Shawnee chief refused to sell the woman and her child. After his death, the chief’s son sold the pair to a trader for $200.

The Shawnee ransomed John Callaway three years later to a trader who brought him to the Boonesborough Fort. Both accounts state that Callaway reluctantly came home as he had assimilated to the culture of the Shawnee. His cousin remained a captive for seven years.  In the Widdice account, Widdice credits Keziah Callaway as stating in an interview that Pawley’s son later came to visit Callaway on a trip out west.

Henry County and the Highlands

John Callaway, 21, traveled to Virginia and married Martha Booker. The couple settled on Callaway’s land grant near present day KY 22. The home was built two years later. Callaway farmed and kept livestock.

Callaway’s solitude and pastoral life lasted for 17 years before he joined the War of 1812.

Kentucky Governor Isaac Shelby commissioned Callaway at 38 as a colonel of the 8th Regiment of Kentucky Mounted Militia in 1813. In Widdice’s account, Callaway had bitterness toward Native Americans after they had kidnapped his sisters, aunt and himself and slain his father. The year before, British forces and the Shawnee chief Tecumseh had decimated Fort Detroit in Michigan. The defeat angered him and felt the need to join the cause.

Callaway reportedly addressed his troops before the battle saying, “…Boys we must either whip the British and the indians, or they will kill and scalp every one of us. We cannot escape if we lose. Let us all die on the field or conquer.”

American troops defeated the British, and Tecumseh was killed in the Battle of Thames in October where Callaway fought. Callaway was offered a promotion to general, according to one source, but refused it.

Callaway returned home in Smithfield to farm and fathered a total 10 children.

The house retains its original construction aside from the front porch that was constructed in the early 1900s. A new edition included second balcony with a narrower porch.

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