1889: The railroad tunnel from Cumberland Gap to Middlesborough is cut through. There is wild celebration on both sides of the mountain.
1891: The Board of Middlesborough City Council is presented with bills for nine pauper burials. The cost for adults is $4.50 and for children $2.50. It is thought by the Council that the number of deaths of paupers in the city “is becoming outrageous and very expensive, it seeming as if paupers from all parts are coming here to die.”
1905: Black Masons from Middlesboro join those from Pineville, Barbourville, London and Altamont for a large picnic in Pineville and the laying of a cornerstone for a Masonic home there.
1919: Drs. Brosheer and Brummet buy the Elks Home on Cumberland Ave. with plans to remodel it for a hospital.
1951: Judge Maddox has written the senate Crime Investigating Committee asking that investigators be sent to Middlesboro “to look into the crime situation, as it might be hooked up with other gambling and dope interests in other towns.”