1. On May 14, 1800, the first Kentucky State Bank was established in Lexington, Kentucky. This bank became one of the most important financial institutions in the state and helped to support the growth of businesses throughout the region.

2. On May 14, 1827, the Ohio and Kentucky Railway Company was incorporated in Louisville, Kentucky. This railway would go on to play an important role in the transportation of goods and people throughout the region and helped to spur economic growth in the area.

3. On May 14, 1861, the Kentucky State Legislature passed a resolution of neutrality in the American Civil War. This resolution attempted to keep Kentucky out of the conflict, but ultimately failed as both Union and Confederate forces would fight on Kentucky soil during the war.

4. On May 14, 1937, the Ohio River flood reached its peak in Louisville, Kentucky. This disaster was one of the worst floods in American history and caused widespread damage to homes, businesses, and infrastructure throughout the region.

5. On May 14, 1988, horse racing legend Alysheba won the Preakness Stakes in Baltimore, Maryland. Alysheba, who was born and trained in Kentucky, went on to win the Kentucky Derby and become one of the most successful racehorses in history.