By Harry Enoch

Many students of history know the first ferry in Kentucky was established at Boonesborough in 1779, and the ferry there continued in operation until the state erected a bridge across the Kentucky River in 1931.

That simple picture, however, hides a world of detail and leaves questions still unanswered today.

The ferry was the brainchild of Richard Callaway.

Callaway, who lived in Bedford County, Virginia, joined Daniel Boone’s party of “road cutters” who blazed the trail into Kentucky in 1775.

Their intention was to settle on the lands Richard Henderson’s Transylvania Company had purchased from the Cherokee Nation, which covered all the area west of the Kentucky River. Boonesborough, the place where they stopped and erected a fort is one of Kentucky’s most historic sites.

Henderson’s claim to Kentucky failed to override Virginia’s interest in the land that became America’s first West.

In 1776, Virginia created Kentucky County, which included most of the present-day state.

Callaway, one of the most prominent figures at Fort Boonesborough, was elected to represent the new county in Virginia’s General Assembly.

During the fall session of 1779, Callaway managed to accomplish two firsts for Kentucky: establishing Boonesborough, the first town and establishing the Boonesborough ferry, the first ferry. The latter was a bit self-serving, as he had the ferry license granted in his own name.

The award came with a condition relevant to our story: the grant “to Richard Callaway, his heirs or assigns” was in effect “so long as he or they shall well and faithfully keep the same.”

The following March, Callaway was killed by Indians while engaged in building his ferry boat.

That leaves us with two major questions: Who actually put the first ferry into operation? And when? Surprisingly, we cannot yet say for certain.

A tangled lawsuit offers the most thorough history of the ferry, but still leaves important details open to speculation.

Callaway left a number of heirs living in Kentucky, so one naturally assumes one of them got the ferry going.

Language in the lawsuit implies as much: “Caleb Calloway & John Holder, who were Administrators of Richard Callaway…did from the time the situation of the County would admitt [until] 1788, did keep & attend the said ferry as the law directs.”

It seems unlikely Holder, who had his own ferry at the mouth of Lower Howard’s Creek, or Callaway actually operated the Boonesborough ferry.

This is implied by another statement in the lawsuit: It “appears, that the said [Richard] Calloway, his heirs or assigns, never kept this ferry, nor manifested a disposition to do it, until about twelve years after the passage of the act [i.e., 1791].”

These contradictory statements might be resolved if Holder and [Caleb] Callaway had others put the ferry in operation on their behalf.

This view is supported by two additional findings in the lawsuit: “It is agreed that John Sydebottom is in possession of the said Ferry, and the land used therefor on both sides of the said River under titles derived from the said Caleb Calloway & others [and] “Caleb Calloway & others have sold their Interest in the said ferry to Robert Clarke & Robert Clarke Junior, under whom Sydebottom claims.” Now we’re getting somewhere.

An explanation behind the lawsuit is in order here.

It was filed by plaintiffs John Patrick and his wife Elizabeth, a daughter of Richard Callaway’s eldest son George who died before Richard.

The defendants were Robert Clark Jr. and John Sidebottom. Lexington District Court found for the plaintiffs who sought to eject Clark and Sidebottom from the ferry operation.

Clark and Sidebottom took the case to the Court of Appeals where the lower court’s judgment was overturned.

The Callaways’ ferry grant was to remain in effect “so long as he or they shall well and faithfully keep the same.”

The high court found this condition was not met, so the grant was voided.

What we can say for sure is the earliest known operator of Kentucky’s first ferry was John Sidebottom. But we still don’t know what year the ferry began operating, the year “the situation of the County would admitt.”

The “situation” may have referred to the difficulty of beginning a ferry operation until Native American raids near Boonesborough had ended.

The Patricks filed their lawsuit in 1798 and the final Court of Appeals ruling against them was not rendered until 1801.

By that time, others had raised concerns about the legitimacy of the Callaways’ ferry grant.

In 1787, the Fayette County Court awarded Capt. Billy Bush the ferry rights at Boonesborough. Bush hired John Sidebottom to operate his ferry.

Since Sidebottom would not have been operating two ferries at the same time, we surmise Bush and Clark must have come to some kind of agreement.

By 1800, Billy Bush gave up his interest in the ferry to his son William Tandy, who applied for a license in his own name from Clark County Court.

After it was awarded, John Patrick sued William T. and got the license revoked on a technicality.

William T. went back to the county court, got the technicality corrected and reacquired the license.

He continued as proprietor until 1824, and having moved to Barren County, he sold the ferry to James Stevens.

The ferry remained in the Stevens family until put out of business by the highway bridge. John Stevens operated the ferry for 50 years. After his death in 1893, his son, Hubbard L. Stevens, ran the ferry.

Ferries today, like steam locomotives and water-powered gristmills, have pretty much passed into oblivion. The last of the many ferries on the Kentucky River still running is at Valley View.

Harry Enoch, retired biochemist and history enthusiast, has been writing for the Sun since 2005.  He can be reached at henoch1945@gmail.com.