The Princess Theatre was originally established in 1925 by George Elam.

Two years later he moved his theatre into a building on Prairie Street where it stands today. Leasing the building from Rowena Ramage, Elam worked to improve the building which was built in 1907.

A new world of entertainment was brought to the citizens of Winnsboro. White silent movies were shown on a screen while live piano music brought the films to life. A few years later Elam bought records to play along with the movies. In 1930, a sound track was added to films and Elam put a sound system in the theatre.

Right before World War II, in the early 1940's, Elam added on to the building, making it longer. In 1960, Elam sold the theatre to Jack Pope. Pope continued leasing the building from Ramage while keeping the Princess operating just as Elam had done. The opening of Monroe's Pecanland Mall in 1985 forced Pope to close the Princess as the Mall Cinema had ten screens compared to the Princess' one.

In 1992, Rowena Ramage gave the Princess Theatre building to the city of Winnsboro. A Board of Directors was appointed to take care of the building. In 1993, the board announced renovation plans to begin immediately on the Princess Theatre.