Grand Avenue Library opened in 1916 as South San Francisco's first library and was one of thousands of new libraries in the United States funded by a grant from businessman and philanthropist Andrew Carnegie. Local teacher Rue Randall Clifford collected the signatures needed for the grant while riding on horseback throughout the city, and in 1914 Carnegie awarded the city $10,000 for construction of a library. The building was designed by architect W.H. Weeks and built by the O'Rourke and Grady Construction Company. It served as the city's only library for nearly 50 years, until a new main library opened on West Orange Avenue in 1966. The building was renovated several times, including completion of a new children's wing in 1953, when the mural "Wynken, Blynken, and Nod" by Gladding, McBean and Company was installed around the fireplace; an interior remodeling in 1985 that created space for more books and moved the main entrance to Walnut Avenue; designation as a local Historic Resource the following year; a seismic upgrade in 1997; and exterior restoration and painting in 2012 to complement the adjacent City Hall building. After another major renovation with a new classroom, outdoor patio, and updated technology, it reopened in October 2016 as it marked 100 years of service to the community.