[5] Osceola is an anglicised form of Asiyahola: assi, from a ceremonial yaupon holly tea or "black drink" and yaholi, the name of a Creek god intoned when the drink was served.

77 of the Ancient Free & Accepted Masons, and the main floor was a bank and hardware store.

[7][8] In December 2023, Osceola City Administrator Ty Wheeler urged residents to switch from using tap water to bottled water as extreme drought affected West Lake.

[9] In February 2024, the Clarke Community School District shut off drinking water in all its buildings due to a severe drought in Osceola.

Amtrak, the national passenger rail system, provides service to Osceola, operating its California Zephyr daily in both directions between Chicago and Emeryville.

[18] The Masonic building was placed on the Iowa Historic Preservation Alliance’s Most Endangered list due to its poor repair and lack of preservation plan.

The China Star restaurant was remodeled and now utilizes both halves of the lower level.

The exterior received an overdue face lift to restore the building to its original appearance.

The front entrances were replaced with a more traditional wood columns and tall glass windows.

The river boat-themed casino has been in continuous operation since about 2000, although it has been bought and sold twice since it has opened.

After a major renovation to the complex, which included a $1 million 132-foot-tall sign along the adjacent interstate, took place around 2006.

The parent company filed for bankruptcy and the casino was sold yet again.

The original and familiar Lakeside name was brought back and the large cowboy sign along the interstate was converted into a slightly smaller, more traditional sign.

A Pilot truck stop was built in late 2010 along the interstate, in place of the former Terrible Casino gas station.