In 1970, developer Roger Benjamin began scouting a site to construct a strip mall featuring Welles, a Midwestern discount department store chain.

Flying over southern Wisconsin, he identified acres of open land in the Town of Harmony along Milton Avenue, between the main downtown streets and Interstate 90.

Benjamin determined that with nearly 200,000 people, the Janesville trading area had a large enough population and sufficient financial resources to support a mall.

Benjamin and two partners created Janesville Properties Company, which purchased 40 acres (160,000 m2) of land adjoining the Montgomery Ward site, and began planning the development.

Plans to construct the $10 million enclosed mall were announced in November 1970 with groundbreaking set for spring 1971.

The mall was remodeled again in 1991, this time featuring a brighter, pastel-based color scheme; the fig trees were removed.

In 1998, the mall was acquired by CBL & Associates Properties, Inc., a real estate trust based in Tennessee.

[11] In 2022, Janesville-based Woodman's Markets proposed adding a 140,000 square feet (13,006 m2) convention center and ice arena to Uptown Janesville in place of the Sears anchor.