A post office was first established at Ocklawaha in 1884. The community took its name from the nearby Ocklawaha River.
In 1935 Ocklawaha was the scene of a shootout between federal agents and Ma Barker and her gang. The feds fired nearly 3500 bullets into the house and the fight ended in the death of all gang members present. Each year, the Ocklawaha Chamber of Commerce puts on a reenactment of the event.