Originally know as Nauvoo, Rolling Prairie remained small town until 1852 when the New York Central Railroad bypassed the larger town of Byron to build tracks through the town. The rialroad brought important changes, increasing trade and commerce and the little town on the prairie began to thrive. In 1853, the United States Post Office was established and the town was renamed Portland. Four years later, the name was changed when postal authorities discovered there were two Portlands in the state. The identity of the postal employee who changed the name to Rolling Prairie is unknown.

Hoover Park (named after President Herbert Hoover) was located at the corner of Depot and Short Streets on an empty lot. In 1937 the country was suffering through the Great Depression. People had little money but plenty of time on their hands. A local resident Corky Llewellyn, a retired circus animal trainer, decided to make an amusement park and zoo, of sorts, on the spot.

South of Hoover Park was the trolley car or Interurban, the railroad that connected South Bend, LaPorte and Michigan City to Rolling Prairie and brought people to watch the free entertainment at Hoover Park. Movies were shown on the sides of buildings and on huge white fabric sheets stretched between light poles.

Long dry summers meant fires and many buildings burned down or were damaged in the early 1900s. In 1942 residents agreed to stop relying on bucket brigades and neighboring fire departments and organize their own fire department. Charles Houseknecht, Charles Hunt, William Ludtke and H. C. Wolcott agreed to lead a campaign which raised $225. Houseknecht purchased an abandoned filling station and turned it over to the township in July, 1946.

The all volunteer unit was put to the test in the early morning hours of Oct. 20, 1963 when the town's citizens were awakened by a deafening blast as two freight trains collided beside the grain elevator. Mrs. Rita Buss, wife of Fire Chief Walter Buss, sounded the alarm for firemen who prevented the blaze from spreading to the grain elevator. The force of the blast was so great it actually moved several inches from its foundation by the blast. Five diesel engines and fourteen cars derailed, flames shot several hundred feet in the air and three engineers were killed, one of them Dennis Culvahouse, born and raised in Rolling Prairie.