Originally opened in 1989 as a joint venture of New England Development and The Pyramid Companies, Emerald Square's original anchors included JCPenney, Sears and G. Fox., with Lechmere added in 1992. The G. Fox store was renamed Filene's in 1993, while Lechmere was closed in 1997 as a result of chain liquidation. Lord & Taylor bought the vacant location in 1998 and doubled the space before its 1999 opening. A carousel was installed in 1999.
Meanwhile, Pyramid had sold its interest in the mall in 1998 to New England Development, which turned around and sold most of its shopping mall portfolio to a joint venture led by Simon Property Group in 1999. Lord & Taylor closed in 2004. The space was assumed by Filene's, which had opened a separate Men's & Home store in 2005. In 2006, Filene's stores were renamed Macy's, as well as the Home & Men's stores.