The Westport Public Library has long been a staple of the community—on Feb. 4, 1886, the Westport Reading Room and Library Association was founded, a charter was given by the state seven years later according to "Westport in Connecticut’s History" by Wakefield Dort (Dort 47).

"Townspeople contributed books, magazines, newspapers, and some money to the original reading room established on the second floor of the Hurlbutt block on State Street. This was open every evening after supper except Sunday; books could be taken out only on Tuesdays and Fridays. There were not enough volumes to allow more liberal rules." (Dort 47).

Frances A. Gray was tabbed as the first librarian of the establishment—she didn’t receive a paycheck. Initially, there were 82 members of the library and membership cost $1 a person.

Eventually, the library outgrew its space and A.S. Hurlbutt offered to rent the ground floor space next to the Saugatuck River for $10 a month with a four dollar rebate after three months. In 1907, a $6,000 fund was developed for the library building (Dort 48).

In 1908, Morris K. Jessup, paid for a brick and stone building to house the library, which allowed the $6,000 to be repurposed into a book-buying fund. After the Westport Library Association was formed, the library received official recognition and the town elected to appropriate $1,000 a year to the library for operating expenses and three library directors to be on the executive committee (Dort 48).