1890: Middlesboro reported a population of 6000. It had seven churches, three banks, a steam laundry, three b rick yards, a foundry and machine shop, the largest tannery in the world, electric lights, 15 miles of railroad around the city and 5 miles of a line up Cumberland Ave. Building improvements over the past ten months total $2,750,000 (roughly equivalent to $55,000,000 today).
1909: The opening ball of the season took place at The Middlesborough with all three ballrooms being in use. Cornwell’s Orchestra from Louisville had been secured for the season.
1910: Lay’s Distilery was totally destroyed by fire. Revenue officers had been investigating some irregularities in the operation of that distillery and others in town.
1927: Final plans were being laid for a big motorcade of businessmen into the Bluegrass for the purpose of advertising the scenic attractions of our area. Fifty-five citizens were already signed up. The Hoe Brothers Quartet was to furnish the entertainment.
1943: Horse and buggy days were coming back due to war restraints on the use of cars. A. P. Lieburg of Middlesboro Steam Laundry was using a pony and wagon for delivery service while Chester VanWinkle of One, Two Three Taxi Service was using a pony and buggy for short hauls.