1897: The newspaper reported that during the Republican primary it was necessary at 10 a.m. to give orders to stop buying votes. It had been ascertained that the votes cast, and those left over, exceeded the total voting population of Middlesboro.
1899: The first commencement of the colored schools was held at the colored Baptist church.
1910: The City Council passed an ordinance to have Cumberland Avenue paved from 17th Street to 25th and 20th Street from Chester to Edgewood.
1928: A Rotary Club organized with L. J. Walls as their president.
1942: Eight tons of scrap iron was collected by the Boy Scouts for the war effort.
1950: The national magazine “Newsweek” ran an article entitled “Corruption—the Middlesboro Mess.” It reported that 176 people were under indictment for offenses ranging from vote fraud and gambling to malfeasance and neglect of duty.
1954: The fifth annual Festival of the Southeastern Kentucky Music Association opened in Middlesboro with 2000 participants. The highlight of the meeting was to be a concert by the 150 voice all-festival chorus.