Watsonville City Plaza rests on a portion of the Bolsa del Pájaro Spanish Land Grant which was owned by the Rodriguez family. This plot of ground in the center of town was given to the people of Watsonville by Sebastian Rodriguez in 1860 through his heirs. In its beginning, it was little more than pastur4e land where cattle grazed at will and children hid from one another behind the tall grasses.

In 1880 a fountain was donated to the plaza by the Butterfly Social Club and in 1893, a drinking fountain was donated by the Women's Christian Temperance Union which wa modernized in 1913. The present bandstand, replacing an earlier wooden one, was designed by architect William Weeks in 1906. A cover was placed on top of the bandstand in 1916 which was designed by Ralph Wyckoff and later replaced in 1965 by one designed by architect Robert Wong.

There has been talk of many innovations to the plaza over the years, but for the most part, it has been left as it was intended to be - a pretty spot in the center of town to be used and enjoyed by the local population.