The history of Olive Hill is the record of a great achievement. It covers a century of progress where a small country village became an important industrial city that can boast of a larger payroll and more carload shipments than any town on the Chesapeake and Ohio Railroad between Lexington and Ashland.
It is fairly certain that very few Indian tribes lived in the area during the time of the white man's exploration and settlement. Rather the abundant game in an unbroken wilderness of hardwood forests made it an ideal hunting ground for the tribes living North of the Ohio River. The many flint arrowheads and spearheads found in and around the region bear evidence of this fact. It was indeed an empty land a waiting inhabitants. During prehistoric times though, many Indians and tribes lived in the region.
Soon after Kentucky became a state in 1792 the pioneer settlers began drifting in. The first house in the Olive Hill area, was built in the year 1800, by Robert Henderson near "Cold Springs" at the eastern boundary of our city. The second house, was built in 1807 by George Henderson, a brother of Robert. It was located a short distance from the first building but somewhat closer to the present city limits. A few years later houses were built on Henderson Branch by Gabe and James Henderson, who were also brothers. The stream was named in honor of this pioneer family.
Thus, the settlement of the area began. It proceeded rather slowly at first, but as the fear of Indian raids subsided the tide of immigration from Virginia and other eastern states rapidly increased. The land was cleared, roads built, and farms and little communities sprang up here and there. The region was originally included in Fayette County, then in Greenup County, and lastly it became a part of Carter County in 1838.
The city of Olive Hill had its beginning as a small country village stretching along both sides of a dusty dirt road. It was located in the section long known as Old Olive Hill, which started just below the present entrance to Sparks Avenue and extended up the hill to the old Dr. Steele place. It consisted of one or more small stores, a blacksmith shop, the Scott Tavern and a few residences.
The town was originally named Oliver Hill by Captain E.P. Davis in 1855 in honor of the oldest citizen, Thomas Oliver. As the name was often slurred in pronunciation and the "r" frequently dropped it was soon changed to Olive Hill--a name to become widely known as a brand of firebrick famous throughout the world and manufactured in Olive Hill by one of our refractories companies.
The first road of any importance through this section was the old state highway from Catlettsburg to Maysville. It was famous as the road over which Andrew Jackson rode in a fine carriage on his way from his home in Tennessee to Washington, D.C., to be inaugurated President of the United States.
The first contract to carry the mail was let to Zachary Tyree. He had to make two trips on horseback each week from Olive Hill to Portsmouth and return. This was a distance of about fifty miles and quite a journey for that day and time. This same Zachary Tyree is credited with having started the first store in Olive Hill. The second store was started by William C. Greer. However, the first general store of any importance was built by Calvin Scott and James Watson.
During the Civil War Olive Hill was burned by the famous Confederate, General John Hunt Morgan, on one of his raids through Kentucky. According to the story, as the General approached the town from the east his raiders were fired upon from ambush by a small band of home guards. Morgan's men returned the fire and several volleys were exchanged. The home guards, greatly outnumbered, soon fled and there were no casualties. General Morgan and his army passed on through the town. Having been informed that this was the home of Unionist Captain James Scott, he and his men as they rode by the Scott residence raised their hats in a salute to Mrs. Scott.
However, when they were camped for the night in the Flannery Bottoms to the west of Olive Hill, the General, still angry because of the attack earlier in the day, ordered his men to return after dark and burn the town. Jeff Williams, grandfather of R. T. Kennard, was a scout for Morgan on this raid and was among those who watched the village burn.