Although Native Americans had doubtlessly roamed the area for centuries, the recorded history of South Miami began at the turn of the century when the rich farmlands of South Dade lured pioneers down through Little Hunting Ground (later known as Coconut Grove) to Big Hunting Ground (now known as Cutler).
In 1897, W.A. Larkins, an early pioneer and founder of South Miami, brought his family into the lush wilderness at the southernmost end of the wagon trail that is now the Ingraham Highway. He started a small dairy and a year later established a post office near what is now Cocoplum Circle.
Upon the completion of the Miami to Homestead extension of the Florida East Coast Railroad in 1906, Larkins bought the property west of what is now Red Road and south of Sunset Drive and established the first grocery and general supply store located in the area. Additionally, the US Government moved the post office to that location, and the surrounding community was named Larkins in his honor.