1890: Meeting held to establish a Masonic lodge in Middlesborough.
1903: Public schools in Middlesboro reported an enrollment of 422 white students and 148 black students. The report complained of problems with overcrowding, poor ventilation and the lack of adequate heat in the schools.
1924: Local agencies sold 1200 cars in the past year. This represented an increase of 25% to 300% for the agencies. The majority of the cars sold for less than $800.
1941: The Middlesboro Stockyards opened near the Tannery.
1952: A “waitress masquerade racket” was thought to be operating in Middlesboro. Women posing as waitresses were being used to lure man into bars and other unsavory places. The main targets were recently returned soldiers “who have ready money.”