The Winthrop Public Library was originally opened on July 8, 1889. The library location was referred to as “Packard Block” in early Town Reports. The original library contained 1,322 volumes at the time of opening and featured a reading room. The collection had grown to 2,700 volumes by 1904. The cost to use the original library was $1 per year, and the original library construction was funded through a combination of private fundraising and a Town grant.

In November 1916, Charles M. Bailey entered into an agreement with the Town of Winthrop to give a new building to be used for library and reading room purposes. The new library was opened to the public on December 2, 1916 in a dedication ceremony that featured president of Colby College, Arthur J. Roberts, and Dennis’ Orchestra of Augusta, Maine. Charles M. Bailey was the best known member of the Society of Friends in Winthrop, and was known for his “Bailey’s Praying Band,” who conducted evangelistic services. Bailey also owned one of the largest oilcloth manufacturers in America at the time, and employed two hundred individuals in Winthrop in the early 1900s. The 1916 structure of rock faced and chiseled granite is still in use today.

Charles Irving Bailey (the elder son of Charles M. Bailey) was the first person to serve as Chair of the newly formed Board of Trustees. Lula A. Clifford was the first head librarian to serve in the new Bailey building, and served to the time of her death in 1940. Clifford’s starting salary was $1 for each afternoon and evening the library was open to the public, and in 1920 was set at $25 per month. Mr. John Stanley served as Town Librarian for twenty-five years (at the Packard Block location) before Charles M. Bailey donated the Bowdoin St. building. John Stanley continued serving on the Board of Trustees and Book Committee after Clifford was hired in 1916. Lula A. Clifford was noted as being Stanley’s assistant librarian prior to 1916.