Madison Julius Cawein was born in Louisville, Kentucky on March 23, 1865, the fifth child of William and Christiana (Stelsly) Cawein. His father made patent medicines from herbs. Thus as a child, Cawein became acquainted with and developed a love for local nature.
After graduating from high school, Cawein worked in a pool hall in Louisville as a cashier in Waddill's New-market, which also served as a gambling house. He worked there for six years, saving his pay so he could return home to write.