James Lafayette Dillard

James Lafayette Dillard (1858-1943) arrived in Winter Garden from Virginia in 1887 with his wife, Mattie Showalter, quickly establishing himself as one of the leading fruit and vegetable cultivators in the area. Immersing himself and his family into the life of West Orange County, Dillard farmed, constructed buildings, ran the town’s garage, founded the Bank of Winter Garden, formed a cigar-rolling business, and was a city commissioner and state legislator, as well. Somewhat of a Dixie renaissance man, Dillard was determined to resurrect his adopted city after the disastrous fires in 1909 and 1912 destroyed much of the central business core. He left his permanent stamp on the life and commerce of Downtown Winter Garden in many ways, most notably through the construction of brick buildings, which survive to this day: the Dillard and Boyd Building (1912) at 12 West Plant Street; the Shelby Hotel (1913) at 1West Plant Street; and the Mann and Mills Dry Goods store (1923) at 31 South Main Street. Dillard also donated the land on which the present First Baptist Church was built in 1922. These solid, architectural jewels were represent his determination to face the future with confidence.