At the Heritage Subcommittee of the City of Springfield Bicentennial Committee meeting in August 1974, Kitty Lipscomb proposed establishing a museum as one of the event's activities. On September 19, 1975, the Bicentennial Historical Museum opened its doors at 311 College Street with Robert Neumann as its curator and director. Supporters soon decided to make the museum permanent.

In 1977, Drury College offered to rent the Bentley House at the corner of Calhoun and Washington Streets to the museum. The renamed Museum of the Ozarks opened in the Bentley House that same year, and purchased the building from Drury two years later. In 1993, the museum sold the Bentley House and moved into the third floor of Old City Hall, where the city of Springfield offered exhibit space at no cost to the museum. The name changed once again to the History Museum for Springfield and Greene County and operated there for over fifteen years.

Requiring more space, the museum moved in 2008 from Old City Hall to Springfield's downtown Square -- the origin and heart of the community. The relocation was a commitment to the continued evolution of Springfield's Central Business District. In 2014, the History Museum on the Square opened temporary exhibits in the Historic Fox Theatre while the former Barth's Building and adjacent building underwent renovation to house the museum. On August 8, 2019, the new facility was opened with more than 18,000 square feet of space for permanent exhibits, temporary exhibits and staff workspace. In January 2020, the museum was named the "Best New Attraction for 2019" by USA Today.

Many people and organizations played vital roles in the development of the History Museum on the Square over the years. The museum gratefully acknowledges the Junior League of Springfield and Greene County Historical Society for their critical support in establishing and growing the museum.