- 1934: Collie Biggers begins construction of the Garden Theatre, and completes the project for $15,000.
- December 1935: Garden Theatre opens with the film SHE, starring Randolph Scott and Helen Galagan.
- late 1930s: a Spanish courtyard theme is constructed for the interior, complete with Romeo and Juliet balconies, lanterns, ceiling stars, and a Spanish tile roof.
- 1940: A Jim Crow balcony is added to accommodate the African American community.
- 1941: Admission price is 35 cents for adults and 9 cents for children early 1940s: state of the art automatic cooling system replaces fans blowing over ice chunks.
- 1955: Carl Floyd Theatres acquires the building, adding a new marquee with flashing red neon, red curtains for the stage, new wide-screen projection equipment, and a repainting of the lobby and box office.
- 1963: The Garden Theatre closes its doors.
- 1964: The Theatre becomes a tractor warehouse for Pounds Motor Company.
- 1993: The Winter Garden Heritage Foundation is formed.
- 2002: The City of Winter Garden purchases the Garden Theatre building.
- 2004: The Winter Garden Heritage Foundation agrees to restore and manage the Garden Theatre.
- July 2004: Winter Garden Heritage Foundation launches a capital campaign to raise funds necessary to rebuild.
- May 2005: Original restoration plans expand to include restrooms in building next door and 3-story support building.
- January 2006: The Heritage Foundation is awarded $500,000 from Orange County Arts and Cultural Affairs, ranked #1 by the grant panel.
- April 2006: The Foundation hires a full time general manager to create an identity, plan programming, and help with construction of the theatre.
- March 1, 2007: the unveiling of the restored marquee and façade.
- January 23-26, 2008: Preview soft opening.
- February 1:First show in the Garden Theatre The Musical of Musicals: The Musical Jester Theater Company.
- February 29 - March 2, 2008: Garden Theatre Gala Weekend of the fully restored Garden Theatre.


