Pikeville sits in the Big Sandy River Valley along the Levisa Fork. Thousands of years before the first European long hunters entered this valley, Paleoindians would have moved through it hunting buffalo, deer, and other game animals. Perhaps a thousand years ago, this area represented the southern limits of the Fort Ancient culture, but by the time Europeans first entered the area in the late 18th century, the Shawnee and the Cherokee made periodic hunting trips along the river, but there do not appear to be permanent settlements from this time.

Early Homesteaders

While there may have been others before him, the first person of European descent known to have passed through what is now Pikeville was Daniel Boone. It was on his first trip into Kentucky in 1767 on one of those long hunts that he passed through the Breaks of the Big Sandy and wintered farther down the Levisa Fork before returning to North Carolina. It is said that around 1790—just two years before Kentucky became a state—Boone led Revolutionary War veteran William Robert Leslie to the spot where Mr. Leslie would establish the first permanent settlement in Pike County.
Pike County was established in 1821 and was named in honor of the western explorer and U.S. Army officer Zebulon Montgomery Pike. On December 30th of 1824, Pikeville was established by the state legislature as the county seat on land owned by Elijah Adkins.
Education was valued early with the first subscription schools being established around 1840. There were sixty-two common schools in Pike County by 1860, and the Pikeville Collegiate Institute—which would grow to be today’s University of Pikeville—was established by the Presbyterian Church in 1889.
Pikeville also saw key events in the infamous Hatfield-McCoy Feud. The attorneys for both sides were from Pikeville and the trial of some of the Hatfields was the first held in the then newly constructed courthouse which still stands on Main Street today. The McCoy family made their home in Pikeville after their home was burned in 1888. Randall operated the lower ferry until his death in 1914, and he, his wife, and other family members are buried at Dils Cemetery, located on the hill just across from the Appalachian Wireless Arena.

Logging and Mining

Prior to 1905, there were few roads and no railroad, so travel into the region was most readily done by river. Pikeville was the last town that steamships could reach traveling upstream. This along with being the county seat quickly turned it into a center of commerce and industry.
Logging was a large industry in the area until the Model-T switched to all metal in the mid-1920s. Huge stands of Yellow Poplar were floated downstream while shipments of tools, goods, and equipment were brought back to Pikeville by steamship.
By the turn of the 20th century, coal mining was expanding throughout the region, and the railroad followed shortly thereafter. The railroad station in Pikeville was established in 1905, and the town continued to be the economic center of the region through the booms and busts of the industry.

The Pikeville Cut-through Project

Because of its location on the Levisa Fork, the citizens of Pikeville were often plagued by spring flood waters which caused millions of dollars in damage. The railroad running through town and the resulting coal trucks contributed to severe traffic congestion among other problems. And land was so scarce that it was choking any potential growth. Mayor William C. Hambley spent decades of his life on a project that came to be known as Hambley’s Dream.
Work on the project begin in 1968 with Pikeville being the first Appalachian town designated as a Model City. In the end, nearly 20 federal and state agencies were involved in the project. The Pikeville Cut-through project moved nearly 18 million cubic yards of soil and rock at a total cost of about 77.6 million dollars. Today, the C&O Railroad, the Levisa Fork of the Big Sandy River, and a modern, four-lane highway pass through the channel formed through Peach Orchard Mountain. The highway was opened in 1987, combining the traffic from four major routes. The project also produced about 400 acres of developable property.

Pikeville Today

Pikeville is home to rapidly expanding regional hospital, a University featuring Colleges of Osteopathic Medicine and Optometry , several local financial institutions including the second largest bank holding company domiciled in Kentucky, and an independent school district that consistently ranks among the best in the state. The city prides itself for its high quality of life with good schools, a healthy economic base, a parks system that provides a variety of active and passive recreational opportunities, diverse offerings for shopping, dining, and entertainment with safe neighborhoods, and an emphasis on quality development and protection of the natural environment.
From an original incorporated area of about three square blocks, the City has expanded to its present size of over twenty square miles.