1. The Battle of Perryville was fought on September 14, 1862, in Perryville, Kentucky. It was the bloodiest battle in the state during the Civil War, with over 7,500 casualties.

2. On September 14, 1923, the Southern Baptist Theological Seminary in Louisville, Kentucky, appointed its first African American faculty member, William J. Simmons. Simmons was a groundbreaking figure in the school's history and helped to diversify its curriculum.

3. On September 14, 1964, Muhammad Ali won his first heavyweight boxing championship by defeating Sonny Liston in a controversial match in Miami, Florida. Despite not taking place in Kentucky, Ali was born and raised in Louisville and later became a cultural icon in the state.

4. Thoroughbred racehorse Citation was foaled on September 14, 1945, at Calumet Farm in Lexington, Kentucky. He went on to become one of the most successful racehorses in history, winning the Triple Crown in 1948 and 16 consecutive races overall.

5. The Kentucky Bourbon Festival, an annual celebration of the state's signature beverage, typically takes place in Bardstown, Kentucky, during the week of September 14. The festival features tastings, tours, live music, and other events celebrating the history and culture of bourbon in Kentucky.