In 1883, a group of men gathered at Ordway, heading northwest looking for homestead sites. Among this group was Captain E.D. Haynes. He was looking for suitable town life. The town was established and named Leola, in honor of Captain E.D. Haynes' small daughter. Haynes served as a surveyor before it was established.

Leola was platted in April and the plat was filed May 1, 1884. The original plat included the area designated for the county seat: bound by Elm Street to the north, Sherman to the east, Main to the south, and Broadway to the west. Leola grew rapidly as more settlers began moving in. The first newspaper, The Leola Blade, opened in 1885. Accompanying business growth was the emergence of such organizations as the Masonic Lodge, Order of the Eastern Star, Modern Woodmen of America, Odd Fellows, and Rebekah Lodge. Throughout the years Leola has had many different newspapers, banks, churches, stores, and theatres.

During the 1920's citizens of Leola enjoyed the new technologies coming to the area. Electrical service was improved and a power plant was added.
Leola celebrated it's 75th birthday in 1959 and celebrated it's 100th birthday in 1984. Leola will celebrate it's 125th birthday in July 2009.

The above information was taken from the 1984 Leola Centennial Book.

Today, Leola is not the bustling town it once was, with fewer businesses and a smaller population than before. However, Leola is a wonderful place to live and a good place to raise a family. Current residents are continuing to work for the future to ensure that Leola remains the beautiful and wonderful community it was and is still today.