1750: Dr. Thomas Walker and his party passed through the Cumberland Gap and camped on the flat land at the foot of the Gap along a creek bank. When Dr. Walker returned to the Virginia settlements, he publicized the Gap as the gateway to the rich lands of Kentucky.
1890: The tomb of Col. Arthur Campbell, famed Revolutionary War hero and early Virginia politician, was unearthed during the excavation necessary to construct 24th Street.
1898: A large crowd was at the railroad depot to see the evening train. Due to the smallpox quarantine, it was the first passenger train to stop in Middlesboro in more than a month.
1918: Pascal Constanzo purchased the barber shop of B. H. Perkins next to Sprague’ Drug Store on Cumberland Ave.
1928: Bob Smith was arrested for moonshining. A longtime resident of the area between Fern Lake and Bartlett Park, he had had an uninterrupted career for many years. The paper noted that he was, “the old-fashioned type who knew his business, and produced a good grade of liquor.
1954: The newspapers reported “blazing mob violence in Middlesboro phone strike.” A crowd gathered in front of the phone exchange and began throwing rotten vegetables against the front door. The next day shots were fired into the phone company coffee room and the crowd grew to an estimated 500, many of whom were throwing rocks at the building. Finally, the telephone exchange was completely closed down. By the next day, strikers agreed that emergency fire, police and health calls could be handled, but there was to be no other phone service.