It could be said that the Orange City Library Association began in 1876 with a group of women meeting in their homes to do handiwork. While they worked, a person would read aloud; it was usually Mrs. Helen Freeman reading as she always brought a book with her. At one of the meetings she requested that everyone bring a book to loan to the next meeting. Thus began the origins of the Orange City Library.

It wasn't until 1879 that the books found a home at the DeYarman Hotel marking the formal organizations of the Orange City Library Association. In 1880, a constitution and by-laws were adopted for a period of 99 years. Mr. A.L. Wellman was the first president and the books were later kept in his store on East Graves Avenue.

In 1884, the books again moved to the drugs store of Dr. Philip W. Hill with members taking turns loaning out the books. Two years latter, the books were move to Dr. Allen's store. As the community grew, a small building was purchased from Dr. Hammond to house the books.

Then in 1892 , Miss. Mary Stillman provided a lot on the west side of Holly Avenue as the new home for the books. It is presumed that the building purchased from Dr. Hammond was moved to the newly donated lot on North Holly Avenue. In 1897, the books moved yet again. This time to the former Orange City Hotel that had been purchased by Miss Melissa Dickinson. She used her own finances to have the structure remodeled into a formal Hall and Library. She later gave the building to the Orange City Library Association. The upstairs of the building was made into an auditorium, while the downstairs was the library with a reading room. A good size dinning room, a fully equipped kitchen and large meeting room was designated for the free use by the women's Village Improvement Association. Gratefully, the building Melissa had donated and largely furnished survived the fire of 1908. When Melissa died in 1910, her absence in the community left a whole in the hearts of her family and friends.

In 1918, Albert and Emma Dickinson initiated plans to construct a new modern library south of the city park. Embarking on building a new library to replace Melissa's building, they contacted Mr. Francis Miller, a Deland architect to draw up plans for a new library. In May 1918, Miller delivered the plans to the Dickinson's. They hired J.H. Bates to supervise the construction of building. In 1919, at the cost of $20,000, the new library was complete. In December of that year, the library was dedicated in honor of Melissa Dickinson, the sister of Albert Dickinson, for her contributions to the betterment of City of Orange City and her unbounding love of the library.