1906: Ground broken for a new $30,000 school building across from City Hall. It was a three story brick structure.
1911: An ad offering Greasy Valley 100 proof corn whiskey for $2.00 a gallon boosts, “We have made whiskey for years and know what it takes to please the people of this section.”
1916: Company H of the Kentucky National Guard was leaving for active duty along the Mexican border.
1922: The Tannery had 165 employees; Big Ben Overalls, 225; J. R. Hoe and Sons, 45; Coca-Cola Bottlers, 8; Chero-Cola Bottlers, 6 and the Ice and Cold Storage Company, 25. The Sel-Hur Wagons Company was turning out two to three wagons a day and the Middlesboro Creamery Company was producing 500 gallons of ice cream and sherbet daily
1952: Newspaper headline: “Main road across mountain to revert to Indian Trail, tunnel to be used as main road? One of the most fantastic stories…out of Frankfort in regard to 25 E.”