1890: Middlesborough broke the record for southern land sales with a total of $350,164 (approximately equal to $6,700,000 today) sold in just 3 ½ hours. There were 1500 to 2000 people in town for the land sales.
1910: Haley’s comet was visible to Middleboro viewers for the first time.
1932: The Middlesboro Welfare Association urged every family with a garden plot to grow twice the amount needed for themselves in order that food be available to orphans and widows.
1935: Greyhound doubled its bus service in Bell County so that there were 6 northbound and 4 southbound buses daily.
1946: The Bell County Citizens League was discussing the county wide laxity in law enforcement, noting that slot machines were readily available in some of the leading hotels.
1951: Pvt. Kenneth Seals of Middlesboro was recommended for the Congressional Medal of Honor.