The initial plan, unveiled in 1958, called for a $7.5 million, five-story mall with a pool in front on the Bardstown Road side and penthouse apartments on the top floor.

[4] The shopping center formally opened on October 10, 1962, in a ribbon-cutting ceremony attended by Louisville Mayor William O. Cowger and Jefferson County Judge Marlow Cook.

[5] On June 21, 1964, an early morning fire that started in the Cherokee Book and Card Stop (also owned by McGaughey) caused $200,000 (equivalent to $1,990,435 in 2023) in damage to the mall.

[11] Inspired by the successful efforts to force positive change in the Mid City Mall situation, many who were involved formed the Highlands Commerce Guild in 1977, which continues to work to revitalize the Bardstown Road corridor as of 2007.

Shortly after the change of ownership, land was leased to allow construction of restaurants in the part of the parking lot nearest Bardstown Road.

The Skyline Chili remains but the other location began as Gatti's Pizza in 1979, became a Dairy Queen in 1997,[12] and Raising Cane's Chicken Fingers in 2015.

It suggested the number of entrances to the mall be reduced and one large one created, where a traffic light would be installed, and this recommendation was carried out 1989.

[17] In 1987, a comedy club called the Funny Farm opened in a space that had previously been Noble Roman's and then Nick's Restaurant.

In 1988, a large thrift store called the Nearly-New Shop moved to the mall's basement,[19] in a location that had previously been a roller skating rink.

Two branches of the Louisville Free Public Library merged and moved into the mall in 1993, occupying a space that had once been a Thrifty Dollar store.