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.

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.

[7] 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.

[7] The Winthrop Masonic Hall (occupying the adjacent land necessary for expansion) was put on the market in 1973, and the library Building Committee requested right of first refusal of the property.

[7] In 2005, the Town of Winthrop purchased the adjacent land necessary for library expansion, and the Board of Trustees hired architect Phil Locashio and began planning.

[11] The library closed on March 6, 2009 when a 16-year-old boy pushed a flaming roll of paper towels into the building's boiler room through a basement window, causing extensive damage.