In 1842, the American Land Company donated a three-acre parcel to the City, naming it Washington Square, likely inspired by a similar park in New York City. The park quickly became surrounded by fine homes and churches, and by 1869, improvements such as lawns, trees, and walkways were added. A Victorian fountain was installed by the 1890s, but the park later fell into disrepair. In 1906, Alderman McCormick, dedicated to revitalizing the area, donated a new fountain and secured funding for further enhancements, which were designed by renowned landscape architect Jens Jensen.
By the 1910s, the neighborhood around Washington Square had become diverse, leading to its nickname, "Bughouse Square," where it evolved into a hub for free speech, attracting artists, writers, and political activists. A group known as "The Dill Pickle Club" emerged, celebrating open expression. In 1957, the park was transferred to the Chicago Park District, and while McCormick's fountain was removed in the 1970s, a restoration plan was initiated in the late 1990s, resulting in a reconstructed historic fountain and various landscape improvements.
