The mall is adjacent to the Meadowbrook State Parkway, making it accessible from the Northern State Parkway and Southern State Parkway. It is a major hub of MTA Long Island Bus, with several bus routes stopping in a terminal area near the southern parking structure.
It was constructed on the site of, and named for, Roosevelt Field, an airport and military airfield where Charles Lindbergh began his historic trans-Atlantic flight. At one time, a plaque at the north end of the mall (in the hall that now connects Dick's and JCPenney) marked the spot where Lindbergh left the ground. Today the plaque is inside the mall, near the Disney Store.
As an airfield, the land served as the take-off site of many famous aviators such as Amelia Earhart and Wiley Post. Charles Lindbergh's solo translatlantic flight took off from Roosevelt Field in 1927. The field was originally named Curtiss Field and was renamed in honor of Theodore Roosevelt's son Quentin, who died in World War I. After the airfield was closed in 1951, the site was developed by New York's William Zeckendorf and designed by I.M. Pei.
Ground was broken on the $35 million project in April 1955. The center opened with a single level and was an open-air center. It included F.W. Woolworth 5 & 10 store, Walgreen Drug, Food Fair supermarket, Buster Brown Shoes, a public auditorium and an indoor ice rink. The original anchor of the mall was a 2-level 343,000 ft² (31,900 m²) Macy's which opened on August 22, 1956.
In 1962 a 250,000 ft² (2,320 m²) Gimbels store opened (today, the structure houses Dick's Sporting Goods and Bloomingdale's Furniture). With the addition, the complex held over 1,000,000 ft² (92,900 m²). A major extension was completed in 1964. Macy's had a 85,000 ft² (7,900 m²) third level added. In 1968 The Century Roosevelt Cinema began operation. At that time the mall was enclosed.
In 1972 a second major expansion was completed which added a 3-level, 260,000 ft² (24,200 m²) J.C. Penney and a 2-level 31,400 ft² (2,900 m²) Alexander's. La Petite Mall, a Tudor-style expansion was built in 1974 that architecturally reinforced the novelty of shopping indoors.
An upper level of stores and food court was established in 1993 after a major renovation which started in 1991. When Alexander's went bankrupt in 1992, Abraham & Straus gutted the building and extensively renovated it, opening in 1992. The Abraham & Straus location at Roosevelt Field only lasted until 1995, when the chain became defunct. The store was slightly renovated, and re-opened as a Bloomingdale's in 1998. The Bloomingdale's store at Roosevelt Field had a major renovation, which was finished by the summer of 2009. The Gimbels anchor was a Stern's between 1987 and 2001.
After Stern's closed, the spot was taken over by Galyan's, which opened in 2003 (later bought out by Dick's Sporting Goods in 2004). Dick's Sporting Goods occupied the eastern section and Bloomingdale's Furniture Gallery, which opened in 2004 and occupies the western half. A new, 3-storyNordstrom and a 2-story wing leading to the new Nordstrom opened in August 1997. Simon Property Group took ownership of the mall when they had acquired Corporate Property Investors in 1998.