It all started with a stand-alone Jordan Marsh store in 1969, built in the middle of what had been woods and a pig farm. It expanded to an enclosed mall on 65 acres two years later. The Maine mall officially opened in 1971 with 21 more stores and a new Sears & Roebuck Co. In 1975, Payne road was renamed Maine Mall road. The mall had subsequent expansions and major renovations over the years, including an addition in 1983-84.

This expansion more than doubled the mall's total retail outfits to 122. A new wing was added for 60 new stores and 3 major department stores: Porteous, Filene's and JCPenney. 

In 1994, the mall received a $6.5 million renovation. A new food court now holds seating for 500 people. Then, Porteous closed their Maine Mall location. In spring 1994, Lechmere was built in a new section between Sears and Jordan Marsh. Jordan Marsh stores were later acquired by Federated department stores.  The company renamed its northeast stores to Macy's including the Maine Mall store in April 1996. Porteous was torn down in 1996 and rebuilt into a 2-level building with Sports authority, on the upper level, and Filene's, that was on the lower level.

In 1997, the major stores were Macy's, Sears, JCPenney, Filene's, Lechmere, Woolworth and The Sport Authority. There was a Filene's Basement in a stand-alone building aside the Mall.

That same year, Woolworth Corporation closed all their remaining stores including the one at the Mall. Montgomery Ward Co. also closed their Lechmere stores division. Best Buy opened in that space in October 1998, David's Bridal took the remaining part of Lechmere in 1999. That same year, Linens'n Things opened in the vacant Woolworth.

The mall owns most of the retail property and the surrounding parking lots at the site, although Macy's and Sears own the land on which their stores sit. Today, the mall has nearly 140 stores located in 1.2 million square feet of space. There is more than 6,000 parking spaces around the mall. 

With the merger of Federated and May department stores, many Filene's and other brands have disappeared. Because Macy's and Filene's both had a store at the Maine Mall, one had to be closed and it was Filene's. The Filene’s Home Store (below Sports Authority) has also closed. This created large vacant spaces at the mall.

In May 2006, General Growth Properties purchased the main Filene's store, which contained 125,000 square feet of space, and the men's/home store, which had 41,000 square feet of space. At one point, the Mall was supposed to get through a major redevelopment. The Maine Mall Cinemas across the street closed.  Best Buy was slated to move to that location. The future former Best Buy was to be rebuilt into a new wing and main entrance for the mall. It never happened and now, General Growth Properties has filed for bankruptcy protection. The Maine Mall will keep on going as it’s located in one of the most dense retail area of northern New England.

In 2010, the economy was still hurting the Maine Mall. Filene's was still vacant and there were many empty storefronts in the mall including the former Linens'n Things. Across the street the planned expansion was halted and the land was sitting vacant since all buildings were demolished. Near the mall, a former Tweeter and Office Max stayed vacant for months. In 2011 Borders closed after the company's bankruptcy. 

Finally good news happened in December 2012 when it was announced that The Bon-Ton would open in the former Filene's space in 2013. New stores started to open at the mall. Book-A-Million eventually replaced Borders and things were looking up. Unfortunately, The Sports Authority went out of business and closed in 2016. The Bon-Ton did not last long as it closed in 2017. In the meantime, the property across the street became home to a new Tru by Hilton hotel and a Carmax.