Between 1922 and 1923, the Cherrydale League of Women's Voters and the Patrons League formed what was then know as the Cherrydale Community Library. It opened in a room at the old Cherrydale School, located at Lee Highway and N. Nelson Street.

In 1931, Supervision of  the Cherrydale Community Library was put in hands of the Library Committee of the Cherrydale Parent Teacher Association. Books were available one day a week through volunteer services of the P.T.A.

In November 1934, County Manager Roy S. Braden asked several interested residents to help in an effort to better support Arlington's existing libraries, and in July 1936, the Department of Libraries was established. The County Board voted $3000 for libraries in County budget and the Department of Libraries became an official County bureau to be run by a County Librarian. The five libraries - Arlington Community, Aurora Hills, Cherrydale, Clarendon and Glen Carlyn - became part of a system serving a County with a population of 40,000 and 74 farms. Funds were allocated so each library received $250 to buy two encyclopedias and an unabridged dictionary as well as other tools.

In 1938, responsibility for the Cherrydale Community Library was transferred to the Cherrydale Library Association, and the Library moved to 3828 Lee Highway.

On Jan. 30, 1941, the Cherrydale Library moved into second floor of Fire Department Building at 3900 Lee Highway.

In 1942, the County formally accepted the Cherrydale Library as part of Arlington County Library system, and on October 2 of that year, the branch moved to 4010 Lee Highway.

In July, 1946, the Cherrydale Branch Library moved to the front half of frame house at 4006 Lee Highway, a former Health Department children's clinic.

On September 4, 1960, ground broke on the site for the new Cherrydale Branch Library at 21500 Military Road, the old "Dudley Property," using J. Russell Bailey, the same architect who designed the new Central Library - making Cherrydale the first Library  branch built by Arlington County. For three years previous, a committee representing Cherrydale community groups had lobbied the County Board some 50 times for the new building (although the neighborhood had also opposed suggestions to relocate the branch to nearer the intersection of Glebe Road and Lee Highway).

The current Cherrydale Branch Library building was dedicated on August 14, 1961.