1. On September 16, 1810, Kentucky became the first state in the union to establish a group of elected officials to oversee the education system. This group was called the Board of Education.

2. In 1824, on September 16, Henry Clay, the famous statesman from Kentucky, was elected Speaker of the United States House of Representatives for the first time.

3. On September 16, 1861, the Battle of Cumberland Gap took place in southeastern Kentucky during the American Civil War. The Union forces under General George W. Morgan defeated the Confederate forces commanded by General Felix K. Zollicoffer.

4. In 1894, on September 16, the Kentucky State Fair opened in Louisville for the first time. It has since become one of the largest state fairs in the country.

5. On September 16, 1992, the United States Postal Service issued a commemorative stamp honoring Mary Breckinridge, who founded the Frontier Nursing Service in Kentucky in 1925. Breckinridge was a pioneer in rural healthcare and midwifery in the Appalachian region.