Winter Garden was settled in the 1850s and the town was established in 1908. Like many Florida towns, it grew when the railroad arrived in the 1880s. The early town consisted of scattered farms and homesteads along the south shore of Lake Apopka. The economy was based on the citrus and vegetables the farmers grew. At the turn of the century a small commercial district emerged along Plant Street and from that residential neighborhoods began to appear.
The historic district is made up of 26 buildings from 1890 through 1945 with most building dating between 1915 and 1940. The entire historic district is 100 acres bounded by Woodland, Tremaine, Henderson, and Lake View Streets. This district was added to the U. S. National Register of Historic Places on August 1, 1996.
The historic district has maintained its Old Florida charm while providing today's visitors with a number of shops, museums, art galleries, breweries, and restaurants to visit. In the center of the historic district is Centennial Plaza where there is a fountain with swings around it. The clock tower is also another landmark in the downtown area. On Sundays there is a farmers market.
During my visit the downtown was beautifully decorated for the holidays. A large tree was set up and the whole downtown was covered in lights. Several areas were set up so you could take pictures. I even spotted Santa. My time in this lovely town was short but I saw enough to make me want to come back soon. read more