Westlake Park is considered Seattle's "town square",[3] and celebrities and political figures often make appearances or give speeches from the four-story shopping center's balcony.

[6] The southernmost block of Westlake Avenue (between Pike and Pine) was closed to traffic in the early 1960s to construct the original southern terminus of the Monorail.

This arrangement continued from the time the Monorail opened in 1962 (in conjunction with the Century 21 Exposition) until the construction of the current mall and park.

[13] In the mid-1990s Westlake Park was the site of a string of guerrilla art pranks led by Jason Sprinkle and the Fabricators of the Attachment, culminating in an infamous bomb scare incident that closed off several downtown blocks.

[15][16] Diagonally across from the park at 4th and Pine, until its closure in February 2020, was a Macy's department store—another designated landmark building, having once been the flagship store of The Bon Marché chain.