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Major George Stockton of Virginia and his half-brother, Colonel John Fleming traveled down the Ohio River by canoe in 1776 and were among the first explorers here. From the time he was an infant until he became an adult, Stockton was held captive by the Indians of New York. When he returned to 'civilization' in Virginia, he was so accustomed to the lifestyle of the Indians that he grew discontent in Virginia and sought to make his home in the wilderness of Kentucky. In 1787 Major Stockton settled at Stockton Station on the northern limits of Flemingsburg. The first man born in Fleming County was Lake Stockton, who was born in 1788. Colonel Fleming first settled at Strode's Station, but three years later he moved five miles west of Flemingsburg near Fleming Creek and established Fleming Station. In 1791 a fierce battle broke out when a party of Indians stole two children and some horses in Clark County and headed for the Ohio River. Colonel Fleming and a small party of whites pursued them, but were greatly outnumbered and forced to retreat. Colonel Fleming was badly wounded in the fight which took place at what is now known as Battle Run. Fleming died at his station in 1794. Fleming County was the 26th county to be established in Kentucky. Flemingsburg was first laid out as a town in 1796. Major Stockton named Flemingsburg after his brother, Colonel John Fleming, and it became the county seat in 1798.

A third commander named Michael Cassidy established a station about 2 1/2 miles West of Stockton Station and an equal distance from Fleming Station. Within the vicinities of these stations settlers grew crops and raised stock while the garrison kept watch for Indians. Michael Cassidy was of Irish descent, but came to America during the Revolutionary War at the age of 12 and enlisted in the Continental Army. Small in stature, he was known for his bravery and was the most warlike of the three commanders. There was an agreement among the garrisons that no one would fire a shot except at an Indian. Unfortunately, one overexhuberant hunter dressed in Indian garb fired a shot at an owl one night, getting the attention of Cassidy who immediately thought Indians were approaching. Cassidy grabbed his gun and headed in the direction of the shot. He found the man, mistook him for an Indian, and shot him only to discover that he had killed one of the most valuable men in the settlement and his good friend. Cassidy had many encounters with the Indians. He was even captured once and his Indian captors attempted to disect him for their own amusement, but Cassidy whipped all three of them bare handed and made his escape. In 1806 Michael Cassidy was elected as the first senator and served several terms as representative. Cassidy died in 1829 at the age of 74.

The lay out of Flemingsburg is attributed to the influence of the Pennsylvania Scotch-Irish who emigrated from the Ulster area. Stockton and his fellow Scotch-Irish settlers of Fleming County, which included the Finleys, Flemings, Keiths, McGowans, Cassidys, Kennans and McAlexanders, all had ties with parts of Pennsylvania as well as Ulster in northern Ireland. John Finley was a pioneer-surveyor who came to Kentucky in 1773 and settled in Fleming County near Hill Top in 1796. Finley discovered Blue Licks and surveyed the land to the Kentucky River near Frankfort. He served in the Kentucky House of Representatives from 1800-1804. After his death the Blue Lick property was given to his son, David D. Finley, whose grandson was David D. Sousley, the Judge of Fleming County Court in 1908.
Freewill Baptist Church

William Kennan settled in Fleming County in 1792 at the age of 19. He purchased a farm on Fleming Creek where he raised castor beans, which he used to make castor oil at his mill. Kennan was perhaps best known for his speed and ability to jump high. Once, when being pursued by an Indian with tomahawk in hand Kennan leaped over a downed tree covered with brush piled ten feet high and landed safely on the other side. Kennan was the last to leave the battlefield, often rescuing others and carrying them to safety on his back. Among the rescued was Major George Madison who later became Governor of Kentucky. Kennan was only 18 at the time. He later bacame a Baptist minister;and in 1799 he represented the county in the first session of the State Legislature when Michael Cassidy was Senator. Kennan died in 1827 at the age of 54.


Flemingsburg United Methodist Church
The Methodists and The Presbyterians both erected brick churches in 1799. By 1800 the population of Flemingsburg was 124. The first store run by Thomas Wallace and the first hotel run by John Faris were established in 1804 and the city was incorporated in 1812. It was during this period that the mineral springs in the "knobby" portion of the county became popular for their medicinal qualities. A hotel was established at Fox Springs near the Fox Creek. Guests flocked to the area from all around to relax and partake of the spring water. Game was plentiful. And so were the politicians who spent the Saturday before election making speeches, passing out whiskey and 'loaning' money to the voters. Flemingsburg was the only place to vote in the county so elections were held for three days.


St. Charles Catholic Church
Presbyterian Church

Flemingsburg Presbyterian Church 

In time, game in the area became scarce and so did the hotel guests. The hotel ceased to be profitable and was eventually destroyed by fire. Just below Fox Springs is Park Lake, which was originally developed by a stock company for it's members as a get away. At Bell Grove Springs, located near Fox Creek, there was also a popular hotel. It was situated on the main road that led to Virginia and a convenient stop for drovers on the way to the Eastern market. In time this hotel also became less profitable and was sold a number of times before burning.

Flemingsburg Christian Church 

In 1828 Dan McLoughlin became the first man to be hung in Flemingsburg. A court house was built in 1829. In 1833 a cholera epidemic swept the county tragically claiming the lives of sixty-five city residents. The community continued to grow with more churches being erected. A Christian Disciples of Christ Church was built in 1839 and the Baptist Church organized a biracial congregation the following year. In 1854 there was a great drouth and in 1855 the town was struck again by cholera with another sixty-five lives lost. The Episcopalians built a church in 1857; and The Roman Catholics established a congregation in 1850 and held services in a newspaper office until a church was built in 1859.

trainIn 1862 James J. Andrews led 22 Union soldiers into Georgia and captured the locomotive "The General". Following thetrain Civil War, in 1865 the first oil well was dug in Flemingsburg at a depth of 995 feet. However, it was not oil that they found, but gas. Oil was discovered nearby, stimulating Flemingsburg's economy and leading to the construction of a narrow gauge railroad that served the area from 1877 to 1908. On May 10th, 1907 the C.F. & S. R.R. fell thirty-eight feet killing three people and injuring seventeen other passengers. In August, 1908, work began on a broad-gauge road and it was finished December 21st, 1908. The railroad served the area until 1956. The depot building has since been utilized for several purposes including a restaurant and a newspaper office. In 2005 the building was renovated by City employees and currently serves as the City Hall.

Seventy-two years after the cholera epidemic another tragedy struck. In 1905 a major fire destroyed seven buildings in the business district. Herman Chittison was born in Flemingsburg in 1908. Chittison had a long successful musical career, performing on both American and French labels as a soloist and accompanist for Ethel Waters and comedian Stepin Fetchit and trumpeter Louis Armstrong. John F. Day, prize-winning journalist and winner of two Emmy awards was born in Fleming County in 1913.

During most of the twentieth century Flemingsburg's economy depended on agriculture. Manufacturing plant's located in Flemingsburg in the late 1950's and early 1960's. An Industrial Park was established in the 1980's allowing for more economic growth. Three manufacturers are currently located in the Industrial Park and other industrial sites are available. A second Industrial Park is being developed to offer another prime location for manufacturers.

Flemingsburg now has a population of approximately 3100 and is known as the “Friendly town that hospitality built”.