1. On July 27, 1864, Confederate forces under General John Hunt Morgan launched a raid on Lexington, Kentucky. The raid ended in a Union victory and was one of Morgan's last major actions before he was killed in battle the following year.

2. In 1924, the Kentucky Derby was run on July 27 for the only time in its history. The race was moved from its traditional date on the first Saturday in May due to construction delays at Churchill Downs.

3. On July 27, 1953, the Louisville and Nashville Railroad's flagship passenger train, the Hummingbird, made its final run after more than 60 years of service. The train was known for its luxurious amenities and was a popular choice for travelers between Cincinnati and New Orleans.

4. In 1969, Kentucky native Tom T. Hall's hit song "A Week in a County Jail" reached number one on the country music charts. The song, which tells the story of a man serving time in jail for moonshining, was Hall's second number one hit.

5. On July 27, 1999, a rare total solar eclipse was visible from parts of Kentucky. Thousands of people gathered at sites across the state to witness the event, which lasted for just over two minutes.