James L. Dillard's Garage

The rise of the automobile led to yet another commercial endeavor for James L. Dillard. He built this garage near the northwest corner of Plant and Main Streets, just north of the Shelby Hotel. This two-story garage building (no longer standing) was managed by Dillard’s son, Marvin Dillard. To make use of the space upstairs, J. L. Dillard hired a Cuban couple from Tampa’s Ybor City to manufacture cigars. When the business didn’t flourish as hoped, the second floor became the site of the armory. Marvin is shown in the front right-hand seat of the car, next to his father; sisters Gladys and Mabel are seated in the back. Employing his Reo and Mitchell automobiles, Dillard set Marvin up as a taxi driver of sorts, ferrying the young Romeos of Winter Garden into Orlando on Saturday nights.