The legendary history of Cloverleaf Golf Course started before golf was popular. It was one of only five area golf courses built between 1931 and 1951. Cloverleaf is the oldest family-owned and operated 18-hole golf course in the St. Louis area.

The Gabriels purchased the property the course sits on in 1913 and established the Gabriel Dairy Farm. The family lived in a large house where the #1 tee now sits and the current clubhouse was the dairy barn. The family home was built in 1849 as an inn for travelers during their long journeys to Alton. According to history, Abraham Lincoln slept in the Southwest bedroom.

In the late 1920's, while working for the State of Illinois, Paul Gabriel got the idea of turning the dairy farm into a golf course. Upon his return, the family went to work constructing the course. On Memorial Day 1931, the first nine holes were opened.

Since golf was new to the area, Paul kept the business going by putting the customer first, always finding a way to get a set of clubs into the hands of someone wanting to play. During the Great Depression, money was so scarce that Paul would often barter in order for people to afford to play. Soon people were lining up at 4 a.m. waiting to tee off. In order to accommodate the customers, Paul's parents started sleeping in the clubhouse and even cooking breakfast for them.