 Originally called "Orange", the city was renamed Chipley in 1882 for William Dudley Chipley, president of the Pensacola and Atlantic Railroad and Florida state senator from 1895 to 1897

During the cold snap of January 1985, a temperature of 2 degrees was recorded at one of the town's golf courses, making it the second-coldest Florida temperature ever recorded and the lowest January reading for the state.Chipley is located at .According to the United States Census Bureau, the city has an area of , all land.