The site was at one time the location of the Annapolis terminus of the Washington, Baltimore and Annapolis Electric Railway, and was known as the "Best Gate" station, which had three single-ended and four double-ended sidings, where rail cars could be shunted on or off of the single-track WB&A east–west railway which ran to the north–south Baltimore and Ohio Railroad and Pennsylvania Railroad lines. This "Best Gate" station gave the name to the nearby Bestgate Road, which today runs along the northern perimeter of the mall. A free-standing, single-level Montgomery Ward store occupied the site during the 1970s. Following the construction and opening of a single-level mall on the site in 1980, Montgomery Ward became an anchor. Additional anchor stores included Washington, D.C.-based Garfinckel's and Hecht's, both with two levels. The mall was expanded in 1983 with the addition of a single-level JCPenney. Garfinckel's closed in 1990 after the company went bankrupt. The mall was expanded again in 1994 with the addition of a two-level Nordstrom store as well as an expanded food court. In 1998 a two-level Lord & Taylor store opened which was followed by the opening of an 11-screen movie theater. The Montgomery Ward store closed in 2001 and in 2002 was replaced with a Sears store. Hecht's transitioned to Macy's in 2006. Another large addition to the mall was completed in 2007, which included an expansion of the existing JCPenney store. The former Garfinckel's space once housed a two-level Borders Books and Music store which operated during the early to mid 2000s until its closure in 2011. A two-level Forever 21 store now occupies the space. The financially struggling and now defunct retailer Woodward & Lothrop tried unsuccessfully to build a store in the mall in the early 1990s; however, its efforts were blocked by the mall's corporate management, which instead brought Nordstrom to the center in 1994. On November 16, 2017, it was announced that anchor Lord & Taylor would be closing at Westfield Annapolis; it closed in April 2018. On February 6, 2020, it was announced that Sears would also be closing as part of a plan to close 42 stores nationwide. The store closed in April 2020. On May 7, 2020, Nordstrom announced it would be closing 16 stores nationwide. All Nordstrom locations had been closed since March 17, due to the COVID-19 pandemic. The Annapolis location was the only Maryland store on the list and the company stated the closing stores would not ever reopen to the public and will be permanently closed as of July 15, 2020. This left JCPenney and Macy's as the only anchors left.
2006 shooting
On Saturday, November 18, 2006, an off duty United States Secret Service agent was at the mall when he witnessed a fight in progress in the food court. During the attempt to break up the fight, one of the combatants pulled a gun and fired at the agent, wounding him. The agent returned fire, hitting the shooter twice. A third person was wounded in the altercation. A Midshipman from the U.S. Naval Academy ran toward the sound of gunshots and provided first aid for the Secret Service agent. That Midshipman later received the Navy and Marine Corps Achievement Medal. The mall was closed shortly after the incident, with all patrons asked to leave over the public address system. The associated trial lasted until December 2007 and the shooter was sentenced to 65 years in prison.
