In 1969, Jordan Marsh opened a freestanding store, which was the first Jordan Marsh in the state of Maine.
In 1971, the indoor shopping mall and Sears were added.
Porteous, a department store chain based in Portland, Maine opened in 1983 as part of a major mall expansion which doubled the size of the mall. This expansion also added J. C. Penney as well as the first Filene's in the state of Maine.
In 1994 the mall underwent a $6.5 million renovation that added a food court as well as Lechmere, Inc. and a larger Dream Machine, a video game and pinball machine arcade.
Porteous closed in 1996 and was replaced with a two-level structure, containing a Filene's Home Store on the lower level with Sports Authority on the upper level, made accessible by the only mall escalators in Maine, excluding department stores. Jordan Marsh was acquired by Federated Department Stores in 1996; as a result, the former Jordan Marsh at Maine Mall became Macy's.
In 1997, F. W. Woolworth Company and Lechmere both closed; within a year, they were replaced by Linens 'n Things and Best Buy, respectively.
In 2003, General Growth Properties acquired the mall for $270 million.
In 2005, Federated Department Stores acquired the Filene's chain. Due to the presence of an existing Macy's at the Maine Mall, both the Filene's and Filene's home store were shuttered in 2006 to prevent overlap.
In late 2008, Forever 21 and H&M opened in the former Filene's Mens & Home first floor. Sports Authority remained in the former Filene's upper floor. Also, an Apple Store and a Coach, Inc. store opened.
In 2009, Linens 'n Things closed due to the liquidation of the chain.
The former Filene's was occupied by XXI Forever, Super Shoes replaced part of the Linens 'n Things space, ULTA Beauty has taken over the former Vinny T's space, Francesca's Collections opened in summer 2010, and across the street, Chipotle Mexican Grill and Cracker Barrel have opened.
In 2012, the mall Santa Claus was fired for being grumpy.
In 2013, The Bon-Ton announced plans to open a store in the former Filene's space, which had been vacant since 2006. This was Bon-Ton's only store in Maine and joined Sears, Macy's, and JCPenney to become the mall's fourth full-line department store when it opened on September 12, 2013.
In January 2016, Gap, Inc. closed its store at the Maine Mall, along with a store at the Bangor Mall.
In August 2016, Sports Authority closed due to bankruptcy.
On June 13, 2017, it was announced that Bon-Ton will be closing its store in August 2017.
On December 6, 2017, it was announced that Round One Entertainment will be opening in the former Sports Authority space in 2018.
In August 2018, Brookstone closed.