The famous outlaw Jesse James once robbed a bank in Corydon, Iowa in 1871. It was the first bank robbery in the state's history.
Osceola County, Iowa, has a rich history that spans centuries. The area that now encompasses Osceola County was originally inhabited by various Native American tribes, including the Dakota Sioux. European settlers began to arrive in the early 1800s, and by the mid-1800s, the region was being settled by pioneers attracted to the fertile land.

The county itself was established on January 15, 1871, and named after Seminole Indian leader Osceola. The first county seat was in Ashton, but it was later moved to Sibley in 1872. Agriculture played a significant role in the county's early development, with settlers primarily engaged in farming and raising livestock. The arrival of the railroad in the late 19th century further facilitated economic growth and transportation.

Throughout the early 20th century, Osceola County saw advancements in infrastructure and community development. Schools, churches, and businesses were established, and the county continued to thrive as an agricultural hub. However, like many other areas in the United States, the county faced challenges during the Great Depression and World War II.

In the post-war era, Osceola County experienced growth and modernization. Improved farming techniques, technological advancements, and infrastructure projects further propelled its agricultural economy. As the county entered the 21st century, it saw continued growth in agriculture, as well as efforts to diversify the local economy with the expansion of industries such as manufacturing and renewable energy. Today, Osceola County remains a vibrant community that celebrates its rich history while embracing progress and development.

This timeline provides a condensed summary of the historical journey of Osceola County, Iowa.

  • 1851 - Osceola County is established as a county in Iowa.
  • 1872 - The first courthouse in Osceola County is constructed.
  • 1874 - Sibley becomes the county seat of Osceola County.
  • 1888 - The Little Crow Monument is erected in Osceola County to honor Native American Chief Little Crow.
  • 1892 - The Chicago, Milwaukee, and St. Paul Railroad reaches Osceola County.
  • 1901 - The first newspaper in Osceola County, the 'Sibley Gazette', is published.
  • 1919 - Osceola County experiences the deadly Spanish flu pandemic.
  • 1922 - The Veterans Memorial Bridge is constructed in Osceola County.
  • 1941-1945 - Many residents of Osceola County serve in World War II.
  • 1957 - The Osceola County Historical Society is established.
  • 1969 - The Sibley-Ocheyedan Community School District is created, merging several local school districts.
  • 1998 - Osceola County celebrates its sesquicentennial (150th anniversary).