Opened in 1982 as San Mateo Fashion Island, it was originally an enclosed shopping mall featuring JCPenney, Bullock's, Liberty House, and Montgomery Ward as its anchor stores.

The Hahn Company, a California-based shopping mall developer, announced plans to build San Mateo Fashion Island in 1980.

In addition to the four anchor stores, other amenities upon opening included an ice skating rink, a food court, and a multiplex movie theater.

Also as part of this deal, Amfac, then-owners of the Liberty House location, closed the store in order to sell its lease to Hahn.

[7] Terramonte renamed the mall to The Island and sold the vacated Liberty House location to Whole Earth Access, a counterculture retailer based in Berkeley, California, in July 1987.

By 1993, the center was over 80 percent vacant; among the major stores that had closed were Oshman's Sporting Goods, Foot Locker, and Pier One Imports.

By this point, the only remaining tenants were the ice skating rink, theater, Montgomery Ward, and an arcade called Tilt!

[11] San Mateo city council approved a plan in September 1996 for developers to demolish the entire structure except for the ice skating rink.

Other major tenants have included The Home Depot, Toys R Us (now Hobby Lobby), Staples (now Ross Dress For Less), Petco, Bed Bath & Beyond (closed since 2021), Marshalls, Cost Plus World Market, and Sports Authority (now Total Wine & More).