Though the small town of Orangeburg, in southeastern Mason County, is similar to many others in rural Kentucky, its history is often interesting and unique. Nestled between two major water courses and at the confluence of several important transportation arteries, the future site of the community was well known to Native Americans and to Kentucky’s earliest explorers. Situated in the foothills of Appalachia, the area was also located at the extreme edge of the Bluegrass region, and developed a strong agricultural base of small family farms. Settled in great part by natives from Virginia and Maryland who brought their slaves with them, the area bordered the abolitionist strongholds of Ohio to the north and Lewis County to the east. Deeply religious, the area’s residents established some of the earliest churches in the state. A strong support for the value of education led to the establishment of the area’s many schools, culminating in the opening in 1922 of the Orangeburg Consolidated School, which provided much of the community’s identity over the next sixty years.

Today, the town is residential. Most of the business establishments which served the residents’ needs have closed. The school itself became a victim of consolidation. The opening of a modern highway just outside of town has detoured much of the traffic which used to pass through this end of the county. But those who grew up or still live in eastern Mason County maintain their pride in the area’s history and their fond memories of a quiet, rural lifestyle too often lost in the modern day.

The great Ohio was the major route for westward exploration in the mid- to late-1700s. On the southern side of this stream, the Appalachian Mountains presented a formidable obstacle to those wishing to reach the interior of Kentucky. Not until these pioneers reached the mouth of Cabin Creek, just past the notorious "Three Islands" of the Ohio, did they find direct access to the fabled bluegrass region. The present-day site of Orangeburg, about four miles south of this point, was situated along this access route at a place they came to call Stone Lick. The area to the north of the Stone Lick was drained by Cabin, Bull, Kennedy and Goose creeks, all of which flowed into the Ohio.

About a half-mile south of the Stone Lick flowed the North Fork of the Licking River. Named Great Salt Lick Creek by the earliest explorers, in reference to the many salt licks along its banks, the stream was called Nepernine by the Indians, who used it to reach the buffalo and deer hunting grounds in central Kentucky. Kentucky’s earliest explorers, including Christopher Gist (1751), Simon Kenton (1771), and Thomas Bullitt (1773), used the stream to explore the state’s cane lands and to mount expeditions against the Indians. A small stream, often unnavigable to even a canoe, the North Fork (sometimes referred to as the East Fork) was then and remains now an important point of reference. Many land deeds, even to the present-day, list properties as "lying on the waters of the North Fork." The area generally south of the Stone Lick was drained by Phillips’, Mill, Strode’s, Stone Lick, and Indian creeks, all of which drained into the North Fork.

Prior to the arrival of white explorers in the mid-1700s, Kentucky was a generally uninhabited land used for hunting by the Shawnee Indians to the north and the Cherokees to the south. The great Shawnee village of Eskippakithiki, in present-day Clark County, had been abandoned several years before, in favor of a site at the mouth of the Scioto River (present-day Portsmouth, Ohio).

The state at that time was cris-crossed by a series of paths and trails. Many of these were wide, flattened avenues created by the movement of buffalo herds between feeding grounds and mineral springs. Some of these were so extensive as to create graded pathways that were often the only ready access for pioneers traveling to the state’s interior. One of the most famous of these was the old "Buffalo Trace" road from Limestone (Maysville) to Blue Licks and on to Lexington.

However, the other trails were Indian "war roads," and these were substantially different. According to the pioneer Simon Kenton, war roads were distinctive in leading from one Indian community to another and in the marks and blazes upon them, while buffalo roads, wider than war roads, were much more worn down and lacked the identifying marks.

The greatest of these war roads in Kentucky was called Athiamiowee by the Indians, and was used by war parties traveling between the Shawnee and Cherokee. White explorers referred to it as the Warriors’ Path, and it was shown by this name on the first printed map of the state by John Filson in 1784. Though it had many branches and forks, the main trunk of this war road led from the mouth of Cabin Creek on the Ohio River, through Mason County to the Upper Blue Licks, past the former site of Eskippakithiki (called by the whites Indian Old Fields), and eventually on to the Cumberland Gap. For both Indian and white explorers alike, this route from Cabin Creek would have been one of the first points along the Ohio River from which relatively flat and easy access to the interior of the Kentucky would have been available.

In their History of Kentucky Lewis and Richard Collins describe the mouth of Cabin Creek as "a noted crossing place for war parties of Indians over the Ohio river. Two roads led out to the Upper Blue Lick—one always known as the upper war road, the other sometimes called the lower war road…the former was the best known, most distinctively marked in its whole length, and oftenest traveled except in the most active Indian times, when it was avoided for fear of them. James Gilmore and his company traveled this war road in 1775. Col. Calamore’s company landed at Cabin creek, and took this war road out to Lulbegrud creek, in now Clark county, where they raised corn in 1775. War roads were distinguished by the marks and blazes upon them, frequently the rough drawing of wild animals, or the sun or moon…"

In 1816 at Washington, Kentucky, the explorer Simon Kenton gave a deposition for a court case in which he clearly described this road as beginning at the mouth of Cabin Creek, following this creek to a branch of Stone Lick Creek, and down it to a point "near the upper end of Williamsburg [Orange-burg]." Here the road forked, and "the right hand fork, which was plainest, kept down Stone Lick Creek to the mouth and crossed the North Fork of Licking near and below the mouth of Stone Lick Creek. The left hand fork crossed the North Fork of Licking at the mouth of Indian Creek and, although not so large as the other, it was blazed and plainly marked by chops on the trees and bushes cut and bent on each side of the same. The said road led up Indian Creek by or through the lick called Indian Lick, and after passing the lick some distance turned up through some beech and sugar tree lands to where Stockton’s Station [Flemingsburg] has since been made… This road was plainly marked all the way from the mouth of Cabin Creek to the Upper Blue Licks. This deponent was acquainted with the above described roads as early as the year 1775 and has well known them from that time to this."

Kenton was asked the question, "Do you know that Stone Lick was a place of notoriety prior to the year 1780?"

"I know it was known by myself and company and by a number of other companies I conversed with, who traveled that road from Cabin Creek to the Upper Blue Licks; it was considerably traveled and went by or through the lick," he replied.

Question: "Has or has not the North Fork of Licking been a creek of great notoriety as early as spring, 1780?"

Answer: "It was known by all the travelers in that part of the country from 1775 that I talked with and I talked with many."

Many other of the early pioneers spoke of the "Cabbin Creek War Road" in depositions, and certainly all were intimately familiar with the area between its beginnings on the Ohio and its crossing at the North Fork. Though later abandoned when pioneers pulling horse-drawn wagons preferred to use the wider, flatter buffalo roads, and long since generally forgotten, the Warrior’s Path played an important role in the early settlement of the state. The War Road continues to be referred to in legal documents and deeds to this day.

A company under the command of Gen. William Thompson of Pennsylvania landed at the mouth of Cabin Creek in 1773 and conducted surveys along Mill and Lee’s creeks. Though "the course of surveys was quite extensive, and embraced the rich lands on the North fork of Licking, and its tributaries," we can only speculate that the explorers traveled the war road and became familiar with the Stone Lick.

Perhaps the first documented trip along this road was that of Col. Robert Patterson’s company in 1775. Patterson (then 22 years old), along William McConnell, David Perry, Stephen Lowry, Francis McConnell, Jr., Francis McConnell, Sr., John McClelland and one other man, "late in October, 1775, left the neighborhood of Pittsburgh for Kentucky, taking their movable property in canoes, and driving 9 horses and 14 head of cattle by land (the first importation of either into northern Kentucky). In November, they reached Salt Lick creek (in Lewis county, Ky., near Vanceburg), where they parted company—Patterson, Lowry, Wm. McConnell and Perry, under the piloting of the latter, striking across the country with the animals, while the others went down the Ohio river to the Kentucky and up that stream to Leestown (one mile below Frankfort). The land party went up Salt Lick to its head, crossed Cabin creek, passing the Stone Lick (Orangeburg, Mason co.), May’s Lick, to the Lower Blue Licks—where they met with Simon Kenton and Thos. Williams, who knew of no other white persons in the country…"

1776 saw the formation of Kentucky County from eastern Fincastle County, Virginia. The area of Kentucky which would later become Mason County "was a virtual hive of settlers in 1776. Varied were the types of Virginia, Pennsylvania and Maryland adventurers who entered the mouths of Limestone and Cabin creeks."

"Mason county fairly swarmed with visitors and ‘improvers’ from Virginia and Pennsylvania—in most cases, of the latter class, many of whom came to select their future homes, while others ‘improved’ for friends or for speculation…these improvements varied greatly; from deadening a few trees and marking initials upon them, up to a log cabin, sometimes covered with bark, but generally uncovered, clearing a patch of ground and planting corn. The men remained generally from two to four weeks."

In April of that year Major George Stockton, Col. John Fleming, Samuel Strode, and William McClary descended the Ohio River, and landing at the mouth of Salt Lick Creek in present-day Lewis County, proceeded into the country towards the Upper Blue Lick, and made improvements along the North Fork and on Fleming Creek. They also improved for Strode, in Mason County, the spot on Strode’s Run where he afterwards settled [in 1785] and had a small station.

That summer, Richard Masterson’s company made several cabins and deadened trees, mostly on the south side of the North Fork, along Mill and Indian creeks. Mercer Beason claimed a preemption of 1,000 acres based on an improvement "lying on a branch of Licking Creek, one mile east from Samuel Strode’s land."

In response to the influx of settlers, Shawnees from north of the Ohio went "upon the war path…The spirit of ‘improving’ was lost in the prudent regard for personal safety…the whites were compelled to constant watchfulness. Exposure without great care was to court almost certain death by the rifle and tomahawk, or by the gauntlet and fire. So few white men visited this county [in 1777], and so great and pervading was the danger, that even that fearless woodsman and great lover of the wilds of nature, Simon Kenton, ‘from 1777 to 1781 generally resided on the south side of the Kentucky river.’"

In July, 1776, Shawnees traveled along the war road to Boonesborough, where they captured the 14-year old daughter of Daniel Boone and the adult daughter of Richard Callaway. The women were recaptured, uninjured, the next day, in what was to become one of the most famous stories of Kentucky’s pioneer history.

In response to the Indian attacks, Maj. George Rogers Clark obtained, by order of the Council of Virginia, 500 pounds of gunpowder for the relief of the settlers in Kentucky. In October of 1776, while Bryan’s Station (near present-day Lexington) was under siege, Robert Patterson was sent to Fort Pitt to procure the powder. The powder was brought down the Ohio and secreted at the Three Islands in what is now Lewis County, near Manchester, Ohio, and about 11 miles above Limestone (Maysville). Col. John Todd and a party of men were sent after the powder, but they were attacked on Christmas day near the Lower Blue Licks and abandoned the expedition. In January, 1777, Col. James Harrod at Harrodsburg raised a company of about 30 men to go after the powder. According to Collins’ History, "they went by McClellan’s fort (now Georgetown), the Lower Blue Lick, and May’s Lick; then turned to the right a little, and struck the Ohio at or near the mouth of Cabin creek. After securing the powder, it was proposed to return by the war road leading from the mouth of Cabin creek to the Upper Blue Lick; but by the advice of Simon Kenton, who discovered signs of danger, they went down the Ohio several miles, and took through the woods until they struck the buffalo road leading from Limestone to the Lower Blue Lick, and returned to Harrodsburg over the route they had come."

Though settlement of the area virtually ceased from 1777 until about 1782 because of the Indian reprisals, the Warrior’s Path through the Stone Lick remained an important travel route for both Shawnee war parties and pioneers.

In February, 1778, Col. Daniel Boone was taken prisoner by the Shawnees near the Lower Blue Licks. After effecting the release of 27 of his men, he was taken prisoner to old Chillicothe, Ohio. Of this trip, Collins’ History states that "Daniel Boone himself passed along Stone Lick, in the eastern end of [Mason] county, in Feb., 1778." In June, Boone made his escape from a party of 450 warriors which had assembled for an attack on Boonesborough, and reached that community in just ten days, no doubt using the Warrior’s Path for this return.

In October, 1780, immediately after Boone’s brother Edward was slain by Indians in what is now Bourbon County, Boone and a party of sixty men pursued the Indians through the eastern portion of Mason County to the Ohio just below the mouth of Cabin Creek, and then returned to their stations by way of the "road leading from the mouth of Cabbin Creek past the Stone Lick."^,

In November 1780, Kentucky County, Virginia, was divided into three counties, including Fayette, with John Todd appointed colonel, Daniel Boone lieutenant-colonel, and Col. Thomas Marshall (father of the great Chief Justice of the U. S.) surveyor.

Robert Patterson, one of the first pioneers to explore the area about the Stone Lick, had a long and illustrious military career. In April 1779 Patterson commanded an expedition of twenty-five men to build a garrison north of the Kentucky River. They built Fort Lexington to defend themselves against British and Indian attacks during the last year of the Revolutionary War. The blockhouse was the first permanent settlement in Lexington, where Patterson also built the first house. He was elected a city trustee for seven terms. As a colonel, he was second in command in the Battle of Blue Licks on August 19, 1782. He later served in campaigns against the Miami (1783) and Shawnee (1786) Indians which secured the safety of Kentucky settlements.

In 1788 he formed a partnership to settle Cincinnati and received one-third ownership in the town site. He died in 1827 in Dayton, Ohio, where he had moved in 1803, after selling his Kentucky land holdings.

Patterson, one of the founders of three cities, had his first glimpse of the wilderness country along the Warrior’s Path where our community stands today.

Late in 1779, the Commissioners of the District of Kentucky held court in the wilderness to adjust titles to unpatented lands, and in a record of the proceedings of these court sessions are found claims of many of the improvers who marked claims in the years 1775 and 1776 in the area which would later become Mason County. However, permanent settlement of the area around the Stone Lick was still on hold, awaiting resolution of the Indian conflict (which was, in effect, part of the larger conflict surrounding the American revolution against British rule).

In addition to the Indian problem, however, those still living in the state had to contend with "the hard winter." Collins’ History states that "the most severe season of cold ever known in Kentucky [through 1873] and the neighboring States was the winter of 1779-80. It is still known as the ‘cold winter.’ The degree of cold reached does not seem to be recorded…In the interior of Kentucky…from the middle of November to the middle of February, snow and ice continued on the ground without a thaw, and snowstorms, accompanied with bleak, driving and piercing winds, were wonderfully frequent. Not a drop of rain fell; the rivers, rivulets, and springs were all frozen solid, and water for drinking, cooking and washing was obtained only by melting snow and ice. All through the hours of the night the slumbers of the suffering pioneers were disturbed and broken by the roarings and strugglings of herds of distressed buffaloes and other wild animals, who fought and bellowed, and strove to reach positions of shelter from the winds and of warmth against the chimneys of the rude log-houses. Myriads of bears, wolves, buffaloes, deer, and other wild animals, and birds and wild fowl, were found starved and frozen to death."

In 1780, only a few authorized settlements were made in Mason County. The number slowly increased in 1781-83, until a flood of surveys were made in 1784-85, in numbers corresponding with those of 1776. Collins’ History indicates that fortified possession of Mason County was not established until the summer and fall of 1784. "Once taken, it was never relinquished; the power of the Indian was broken; his hunting ground, this favorite portion of it, was gone. Possession was not yielded without a struggle. Although the stations in this region were never regularly besieged, as had been the whole circuit of stations in the interior, from 1777 to 1782, yet Indian forays for murder and horse-stealing were common." Despite the great influx of permanent settlers, Indian incursions and raids continued to be a threat to Mason Countians until the summer of 1793.

Even in the face of such hardships, the settlement at Lexington continued to grow. After the Revolution, town leaders laid out streets and lots. Among the first lot holders, on December 26, 1781—when the plan of the town was adopted and the lots disposed of—were "Francis McDermid" and George Shepard.

If anyone can be said to be the founder of Orangeburg, it might be Francis McDermed, Sr. McDermed had little hand in the beginnings of the actual township, and in fact died a few years before its establishment. But it was he who laid claim to the land which now makes up the community, and it was his children (and their spouses) who shortly after his death developed and named the town.

McDermed is a shadowy character, somewhat lost to history, and perhaps has not received the credit he deserves for his involvement in the state’s early settlement. Partly because of the loss of many Fayette County public records which burned in 1803, researchers seemingly have overlooked the major role that McDermed and his family played in the establishment of the city of Lexington. But before settling in central Kentucky, McDermed explored the area around the Stone Lick, and found the land there desirable enough to enter a claim under his own name.

Little is known of McDermed prior to his arrival in Kentucky. Several of his children were apparently born in Prince William County, Virginia, including his oldest child, Francis, Jr., who was born about 1757 and who served in the Virginia militia during the Revolution.

In all probability, McDermed came to Kentucky in 1776 as a member of one of the many companies surveying land in Mason County that year. Perhaps he accompanied the group which improved along Lawrence Creek, one member of whom, in June, 1775, had given the name Lexington to the spot where that city was to be founded in 1779. Perhaps he joined the Bartholomew Fitzgerald party which improved along Mill Creek, and which included a John Williams, likely the same John Williams who would own one of the original lots of Lexington. Most probably, McDermed was a member of Robert Masterson’s company, which improved along the North Fork. Members from all of these parties had strong ties to the eventual development of the city of Lexington.

As mentioned in Collins’ History, many of the Virginians who came to Kentucky came to "‘improve’ for friends or for speculation." McDermed may very well have been among this number, as there is no record of his establishing any kind of permanent settlement where Orangeburg stands today. Rather, his intent may have been to lay claim to lands allocated by the laws of Virginia.

In an effort to regularize western land distribution, the Virginia General Assembly in 1776 devised a system known as "corn patch and cabin rights." The law provided that a settler on western lands could demonstrate a serious intent to establish a claim by erecting a cabin and planting a patch of corn prior to January 1, 1778. This procedure would establish a claim to four hundred acres if the claimant also procured a Virginia land warrant and registered a deed. The law said nothing of the cabin’s size or construction nor of the size of the corn patch, so even a token shelter and a few stalks of corn would qualify. Settlers who erected buildings and cleared land could apply for "preemption" warrants, usually for one thousand additional acres. To enter a land claim, the statutes prescribed four steps to be completed in sequence: 1) obtaining the warrant; 2) making an entry; 3) surveying the land; and 4) returning the survey and entry to the land office. Afterward, the land office entered a "patent" for the claim. According to the Certificate Book of the Virginia Land Commission, 1779-80, McDermed’s actions in 1776 fit exactly this pattern.

As a cabin had to be erected to secure "preemption rights," we can assume that McDermed’s was the first building erected at what would become the site of Orangeburg. However, as he apparently did not stay and settle there, we can also assume that it was of minimal construction. Like many other speculators of the time, McDermed built his cabin, planted his corn crop and quickly moved on. Later in that summer of 1776, he was known to be making improvements on Hinkston and Somerset creeks in what is now Montgomery County, in the company led by Col. John Crittenden, later a pioneer of Woodford County. McDermed was not considered to be one of the leaders of this party, but was probably employed as a "marker" for the survey company.^, As such, his duties would have been to identify claim boundaries by "driving down stakes or ‘stobs,’ chopping notches on trees and even bushes, turning up stones, and following the meanders of streams and combes of valleys or the watershed of ridges."

McDermed seems to disappear from Kentucky for the next few years. It is possible he returned to Virginia, as few whites lived outside the settlements of Boonesborough, Harrodsburg, and St. Asaph’s during the troubled years of 1777-80. Apparently his family had remained in Virginia, as his son Francis, Jr., enlisted in the Virginia militia in Botetourt County, Va., in about April, 1780. His daughter Sarah’s obituary indicates that Francis, Sr., brought his family to Kentucky in 1779.

Certainly Francis McDermed did return to Kentucky, and was instrumental in the beginnings of the new city of Lexington. The first permanent settlement of the town was the blockhouse established by Col. Robert Patterson and his group from Harrodsburg, in April 1779. McDermed is not mentioned as one of this group, but by March 1781 Francis McDermed, Sr., and son Francis, Jr., were helping Patterson to build a "new" Fort Lexington.

On December 20, 1781, the trustees of the new city met at Higbee’s Tavern and approved the plat of the town, which McDermed had helped to "lay off." When the plan of the town was adopted and the first lots recorded, Frances McDermed was listed as the owner (by drawn lot) of "out-lot" 51, a five-acre parcel which today would be located on the south side of Main Street, near its intersection with Rose Street. Listed as owners of smaller "in-lots" were Charles Williams (No. 54) and George Shepard (No. 50), who were or would become his sons-in-law. Their lots were also located on the south side of Main Street, between Mill and Upper. In exchange for receiving these lots, citizens were "required to pay a proportionable part of the money necessary to build the public houses and expenses arising toward good order and regularity in the town."

Over the years McDermed continued to work, and continued to amass and consolidate his land holdings. Because of defects in Virginia land laws and the many overlapping claims made by pioneer settlers, the state enacted legislation in May, 1781, authorizing the County Courts of the District of Kentucky to direct surveys for the poor people of the land. In each county was appointed an official surveyor, who appointed deputies as needed. By 1784 the state required permanent, accurate surveys of settlements, preemptions and improvements. There was plenty of work for survey teams, and McDermed’s name shows up in several deeds of the period. In March, 1784, Henry Lee, the Deputy Surveyor for Fayette County (of which what is now Mason County was still a part), completed a survey of 750 acres in his own name based on a Virginia Treasury Warrant. The land was listed as lying near John Churchill’s preemption, on the north side of the North Fork. "Francis McDermit, Snr." is listed on the deed as "Marker," and his son Francis, Jr., as chain carrier. Early that same month, McDermed completed a survey for Joseph Moore of 4,000 acres, described as "lying and being in Fayette County, one mile north of the North Fork of Licking at an old Indian Camp on a War Road…"

McDermed had, over the years, maintained the claim to his settlement and preemption at the Stone Lick. That it was well recognized was shown by its mention as "McDermitt’s Settlement and Preemption" in Virginia land warrants issued to Thomas Marshall in January, 1783, by Governor Patrick Henry. Marshall’s massive land grant stretched from near the Stone Lick to the mouth of Cabin Creek, in all 15,000 acres. This was just one portion of the many thousands of acres of land claimed by the Marshall family which would come to encompass vast portions of Mason, Lewis and Fleming counties.

On March 18, 1784, McDermed, having obtained a warrant and made an entry, took the third step necessary to permanently secure title to his settlement and preemption, and had the property properly surveyed. His 400-acre settlement was entered as lying on the "North Fork of Licking." The adjoining 1,000-acre preemption was entered as lying on "Stone Lick," the name given to the watercourse running through and containing the actual salt lick. McDermed then took the final step of returning the survey to the land office, and on May 13th was issued a final deed to his claim.

Meanwhile, McDermid accumulated more land. Military entries were made in his (or perhaps his son’s) name on the Cumberland and Green Rivers. 140 acres were claimed on Haw Creek in Fayette County. Another 1,000 acre tract along Stone Lick Creek, near his settlement, was obtained from Beverly Randolph in 1790.

McDermed’s holdings in Lexington, along with those of his children and their spouses, were extensive, and eventually included the entire block today bounded by Broadway and Limestone Streets, between Second and Third; much of the property along Main Street between Limestone and Rose Streets (on both sides); some of the area now comprising Transylvania University’s campus; and an area near the current courthouse which became known as "McDermed’s Square."

In February 1783 McDermed’s daughter Mary Ann married George Shepard at Fort Lexington. Shepard, one of the original lot holders of the new town, would eventually emigrate to the Stone Lick and become one of the leading citizens of the new town to be established there.

In the Spring of 1792, just weeks before Kentucky was admitted to the Union as the 15th state, Francis McDermed, Senior, passed away. An article in the Kentucky Gazette, the state’s only newspaper at the time, indicated that the large estate he left behind was already causing a rift among his children.

In the absence of a will, a lawsuit arose over the division of McDermed’s estate among his children. The suit was quickly resolved, and by June distribution of the land had begun. Generally, each of McDermed’s children received about 157 acres of the Mason County lands, plus certain lots in Lexington in a balanced apportionment.

Shortly after McDermed’s death, his son Francis, Jr., had married (for the second time) Margaret Redden, and his daughter Camille (Milly) married Gabriel Phillips. As previously mentioned, daughter Mary Ann had married George Shepard. His daughter Catherine had married Charles Williams, who may have been the son of John Williams, another of Lexington’s founders. Margaret was married to Duvall (or DeValt) Cooper; Sarah to Simon Hickey. Daughter Frances, who was married to George Wilson, died shortly after her father, on June 18th. Frances was also the name of the wife of his son Hugh.

Through a series of extremely complicated and tedious deed transfers, the estate of Francis McDermed was divided. A review of these documents sheds much light on both the development of the city of Lexington and the history of the town soon to be known as Williamsburgh.

Since the "wilderness" days of 1784 when Francis McDermed legally established his land claim at the Stone Lick, the country there had changed considerably. With the re-establishment of Simon Kenton’s station late in 1784, the route from Limestone (Maysville) through the Lower Blue Licks became the favored route to Lexington, detouring much traffic from the old War Road. Mason County had been formed, from Bourbon County in 1788, with the county seat at Washington. Kentucky had become a state on June 1, 1792. Settlement had begun in earnest; Mason County reported a population of 206 families by 1787, and the state’s population in 1790 was 73,677, including 12,430 slaves. By 1794, the Indian raids into Kentucky were ended.

Others had staked their claim to the lands of eastern Mason County. Edmund Phillips arrived at Limestone in February, 1785, bringing "his father, Moses Phillips with his wife, their sons, John, Gabriel and Moses, and sons-in-law Peter and William Bryam, and Chestnut Theobalds, their wives and a family of Negroes." The group settled first near Lee’s Station, where in 1787 Moses Phillips’ sons John, Moses and Thomas were ambushed by Indians while working in their corn field. Moses and Thomas were killed and scalped; John was badly injured, but recovered.

Moses Phillips (the elder) by October of 1787 had claimed an 873-acre tract of land (which today would include much of the area between Orangeburg and Rectorville), bounded on the south by the North Fork; on the north by McDermed’s settlement; on the east by the huge Thomas Marshall claim; and on the west by a 504-acre entry of George Farrow.^, Moses Phillips moved to and settled on this property about 1790, and eventually his family "owned nearly all the land on the North Fork from the mouth of Stone Lick Creek to that of Phillips’ Creek." Phillips lived out his life on this property which came to be known as Pea Ridge due to the poverty of its soil.

Moses’ brother John Phillips "moved from Virginia to Kentucky in 1794, landing at Brooks’ Landing. His brother who…was then living on the North Fork, sent his teams for him and his family, the brothers embracing after an eventful separation of eight years. John enjoyed the liberal hospitality of Moses for a short time and then settled on the land [owned in 1876] by the heirs of William Kennan. Here he lived but a few years, and, dying was buried near the bank of the North Fork, exactly where is not known."

John’s son George Phillips came to Kentucky in 1790, locating first in Scott County and then moving to Mason County in 1796. He settled his family on property purchased from Thomas Marshall which adjoined his uncle Moses Phillips’ tract and which was located at the mouth of "the creek which bears his name." Descendants of George Phillips have maintained continuous family ownership of this property to the present day.

Other Virginia land grants in the area were to Richard Masterson, 1270 acres on "the headwaters of Indian Creek" (near where later would be established the community of Mount Gilead); George Farrow, 4,518 acres along the North Fork; George Stockton, 2,000 acres on the North Fork; Samuel, James and John Strode, 3,845 acres on "Strode’s Fork of the Licking River."

Charles Pelham entered claims for land along Bull Creek and Kennedy’s Creek. Pelham, John Marshall and Ebenezer Brooks filed entries for lands along Cabin Creek, adjoining the Thomas Marshall tract. Charles Yancey and Levin Powell did likewise along the North Fork.

Colby Shipp and Horatio Hall established holdings adjacent to that of Moses Phillips, as did Francis Foushee, of Stafford County, Virginia.

Capt. Winslow Parker, son of a distinguished Virginia family, had by 1785 left that state and was living in Mason County. With him (or soon to follow) were his brothers Richard and Harry Parker.

In 1793 and 1794 the children of Frances McDermed, Sr., completed the division of the lands from his estate. In June of 1794 deeds were recorded in each of their names. McDermed’s 1,000-acre preemption tract, a long, rectangular-shaped box of land surrounding what is now Orangeburg, was divided into smaller rectangles, usually of 157 acres each, for each of his children. 100 acres was placed in trust for his grandson Edward.

George and Mary Ann Shepard received a 157-acre tract which lies just west of where Orangeburg stands today, on either side of the old Taylor Mill (Halfhill) Road. Some of the original boundary lines of this property can still be seen in aerial photographs. High on a hill overlooking the town, their descendants have erected an impressive monument to the old Revolutionary War soldier and the daughter of one of Kentucky’s pioneers.

Additionally, George Shepard purchased from the other McDermed heirs a 257-acre tract, just east of the where the town is today. State highway 1234 crosses the southern tip of this property, as does the main branch of Stone Lick Creek. The deed for this transaction states that the property "includes the Stone Lick."

The land on which most of the present town of Orangeburg lies was included in the property received by Charles and Catherine Williams. By 1795 this property had been divided and sold, one piece to their son John, another to Harry Parker, and a 55-acre tract to Moses Bennett. Apparently, it was during this year that Parker and John Williams formally laid out the town of "Williamsburgh" on the site, naming it after John or his family. The original town plat cannot be located, and it is very difficult today to determine their exact plan. However, deeds from the period clearly indicate that at least 48 lots were surveyed. The earliest known mention of the town is in a deed dated September 24, 1795, from Moses and Elizabeth Bennett to Ephraim Cole, of Mason County, which indicates that the 10-acre property lay "where the road enters the out lotts near the town of Williamsburgh." Another deed of the same date from the Bennetts to Cole is for the sale of "one lott of ground lying and being on the main street in the town of Williamsburgh…whereon the said Bennett now lives, known by its No. 14." This lot was sold for £50. From the deeds it appears that both properties were obtained from John Williams’ inheritance, and lie squarely where the town of Orangeburg sits today. Obviously, Moses and Elizabeth Bennett were among the very first citizens of the new town. Bennett continued to actively sell properties in and around the new town for the rest of 1795.

Not until March 1796 did Parker and John Williams begin in earnest to develop the town. Mason County’s public records are filled with land transactions by the two during that year. On September 5th, Harry and Joanna Parker sold lot No. 8, on "Main and Cross Streets," to Frances McDermed, Jr., for £70.

Many of the "in-lotts" seem to have been of approximately one-fourth acre, measured as four "poles" wide by nine deep (a pole being approximately 16½ feet, making the lots about 66 by 150 feet).

Parker seems to have been a property speculator and developer, and records do not indicate that he stayed to oversee the progress of the town he helped to found. Over the next few years, he would move with others of his family to Lewis County.

Among other citizens listed in the town’s earliest deeds were Thomas Dobyns, Aquilla Smith, John Means, Sr., George Means, Hugh Hanna, Adam Stewart, William McSherley, Benjamin Rankins, Cornelius and Lewis Coryell, Ennis Duncan, John Johnston, and Thomas Holt.

By the turn of the century, scores of land transactions had been recorded for the Williamsburgh area. Mason County’s 1802 tax list lists over 100 separate property owners along the North Fork and on Bull, Cabin, Kennedys, Phillips’, Indian and Stone Lick creeks.

By 1814, a post office had been established at Williamsburgh, the first postmaster being Elijah Thornberry, followed by Leroy Ewell, Levi Starkey, and J. W. Tilton.

By legislative act of February 29, 1836, the town of Williamsburg in Mason County became known thereafter as Orangeburg.

Legend says that the reason behind this name change was to avoid confusion between the town and the Williamsburg in southeastern Kentucky, now the county seat of Whitley County. However, further investigation sheds doubt on the legend, as that community was known as "Whitley Courthouse" until 1882, when it was changed to Williamsburgh. This was nearly fifty years after the name change for the Mason County town. The reasons behind the change may be lost to history, but apparently the town was renamed in honor of a prominent local citizen and landowner, Providence Orange Pickering.

The community of Orangeburg was incorporated by a legislative act of February 20, 1860.

Though a thriving rural community by mid-century, Orangeburg had obviously not grown to a great extent, as it was incorporated within the original boundaries set in 1795-96.

Many of the settlers in the area about the town of Orangeburg had brought with them slaves from Virginia and Maryland. The Phillips and Marshall families in particular owned many slaves. One source indicated that George Phillips came to Mason County with "25 Negro children, the most of which died from…cholera and they are buried back of the orchard at what is know…as The Simm’s place."

On the eve of the Civil War, emotions ran high regarding the issue. Church congregations had split, some as far back as the late 1830s.

In the town of Berea, Madison County, the abolitionist Rev. John G. Fee and his disciples were "required" to leave the county in January, 1860, "on account of their anti-slavery principles and teachings." Within a few days "a public meeting at Orangeburg, Mason County, notifies Rev. James S. Davis (a co-worker at Berea…with Rev. John Gregg Fee, whence he was recently preemptorily required to leave) who settled soon after on Cabin Creek, Lewis County, to remove from Ky. within seven days. The meeting approved the action of the Madison County meeting, ‘as necessary and justifiable by a proper regard for the protection of their property and the safety and security of their families.’ Jan. 25, he was called on to give up a large number of copies of H. R. Helper’s Impending Crisis of the South, which he had received for circulation; at first he refused, but finally, by way of compromise, burnt them in the presence of the persons who had called."

For a time after the war Orangeburg had a substantial black community. "A black school was built around 1890 and continued until 1920. At the time, there was also a black church but the black population left the Orangeburg area." Today there are few local residents of African-American descent, but some of those former citizens of our community are interred in the integrated Old Orangeburg Cemetery.

By 1876, the community of Orangeburg had become a thriving small town. A school had been established along the old "River Road" in 1850, and the post office name was finally changed from Williamsburg to Orangeburg. In 1852, rights-of-way were given for the Maysville-Orangeburg-Mount Carmel Turnpike; a resident from that time remembered that Orangeburg, being the half-way mark for the "stage," was where the horses were changed. Main Street was by then the "Salt Lick" Turnpike (toward Vanceburg).

An article about Orangeburg in the November 17, 1883, edition of the Maysville Republican stated that "our little place is well supplied with white sulpher water by Johnson McKay’s spring just on the edge of town. It is similar to the Blue Licks waters in Nicholas and Fleming Counties." A map of the area shows the "public spring" as being just north of the town, close to where the Methodist church is today.

But the term Orangeburg was also used to denote the voting precinct which covered nearly the entire eastern portion of the county. Small communities which were or would become part of this precinct were Springdale, Rectorville, Plumville, Oakwoods, and Bridgeport; Mt. Gilead lay on the border with the Lewisburg precinct. Portions of the east end of Maysville (Woodville and Chester) would eventually fall within this area, too.

For generations to come, the area would take its identity from the Orangeburg school system (finally consolidated in 1912 from the smaller schools of Stonelick, Plumville, Dickson and Mt. Gilead, and later Bernard and Rectorville).

Many residents of the "Orangeburg Precinct" today can trace their lineage back to one of the original settlers of the area or to the children of Frances McDermed, Sr.

The historic Stone Lick Baptist Church, established in 1796, celebrates its bicentennial with the town of Orangeburg. The Olivet United Methodist Church, established about 1825, also continues to thrive. Well-kept local cemeteries pay homage to the pride natives and citizens of the area hold for their heritage.