The History of West Winter Park

The history of Hannibal Square, an excerpt from the Hannibal Square Heritage Center...

Imagine a different time in the days so long ago…

Before air conditioning, before easy travel by air or even road, before “Juneteenth,” and way before the civil rights movement, Winter Park was the first planned community in Central Florida, strategically built around the railroad that served commerce and travel.

Hannibal Square (the “west side”) was officially founded in 1881, only 40 years after Florida became the 27th state, and 14 years after the state reentered the Union after seceding and co-founding the Confederate States in 1861.

The free black families who lived here provided a ready source of labor for building a town to serve wealthy white winter residents and visitors. Although Florida and Winter Park were to stay deeply segregated into the 1960s, the non-agricultural railroad jobs and domestic service positions with Winter Park’s wealthy white families resulted in educational opportunities and comparative prosperity and privilege for Winter Park’s black residents.

​On October 12, 1887, young Republican Gus Henderson lead a march of black registered voters across the railroad tracks to Ergood’s Drugstore. The Oct 12, 1887 election was held during the day. This established the quorum, which then voted to incorporate the town of Winter Park, which included Hannibal Square, in its boundaries. In addition, two black men from Hannibal Square, Walter B. Simpson and Frank R. Israel, were elected Aldermen and served from 1887 to 1893.

​From its beginnings, Hannibal Square was rooted in faith, family, and community. The west side was characterized by high levels of education, business and home ownership, and by professional standing among its black residents.

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