Mrs. Elinor Cochran Stewart donated 125 books to form the core of a lending library at Gloucester Woman’s Club, Long Bridge Ordinary between the years 1914-1918.

By 1925, the library was relocated to the County Clerk’s Office.  When the collection totaled 2,000 volumes the library moved again to the offices in the Bank of Gloucester. 

In 1933, a bequest of $10,000 by Mrs. Stewart provided the basis to purchase land and construct the original Gloucester Library.  The Library was formally dedicated June 27, 1935.

A children’s wing was added in 1956 principally through the efforts of Stuart W. Jackson.  The Virginia Room was funded by a contribution from Mr. and Mrs. George H. Cunningham in 1973.

In 1985 the Gloucester Board of Supervisors appropriated $29,000 for fiscal year 1986, and the library qualified for state and federal grants. 

On October 20, 1985, the first Point Branch Library opened in the Tidemill Center.

A 3500 square foot expansion was added to the Gloucester Library and dedicated October 25, 1987 due in large part to the help of Mr. Henry A. Schutz serving as President of the Board of Trustees for the Library and the Gloucester Library Endowment Foundation.

The Point Branch relocated to its present location and was dedicated on April 11, 1992.

The Bookmobile began operation in 1993.

The Library system became automated in 1999.

The Gloucester Library upgraded to a 24,000 square foot facility when it moved to its present location in the Main Street Center and was dedicated June 5, 2004.