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Winter Park Library Archive

Hannibal Square

Hannibal Square is one of the oldest officially recognized neighborhoods in Winter Park. Along with the western half of the city, this neighborhood is historically the home of Winter Park’s Black/ African-American Community.

The West-Side’s thriving community was purposefully established by Loring A. Chase to create a permanent settlement of African-Americans to act as hired help and laborers to support the wealthy vacationers to whom Winter Park was marketed. It’s primary block, Hannibal Square, was named for – as put by Chase, himself - “the great African general”.

However, those who made Winter Park’s West-Side their home were far more ambitious than Chase had designed, and many began their own businesses ventures and many opted to participate in the newly forming town government. This development was further facilitated by Winter Park’s largest voting block being the West-Side’s African-American residents, a rare occurrence during the Reconstruction era.

The West-Side’s civic participation was not well tolerated by many of their white neighbors, who campaigned to not include Hannibal Square as part of the town during its incorporation in 1887. The effort failed, as a result Hannibal Square was included as part of the town’s original boundaries. Another result of Hannibal Square’s inclusion in Winter Park’s incorporation was the election of the only two African-American aldermen to serve in on the town’s city council – Walter B. Simpson and Frank R. Israel. They both served until 1893 when William C. Comstock led a successful petition to request that Hannibal Square be removed from Winter Park’s boundaries by an act of state legislature.

Hannibal Square would not be considered a part of Winter Park again until 1925, when the West-Side’s vote once again would be required to elevate the town’s designation to “city”.

Hannibal Square boasts some of Winter Park’s most fascinating history. 

West Side Collection

To learn more about Hannibal Square and the West-Side, click the leaf to check out our West-Side Collection.

Hannibal Square Library

Be sure to also visit:

Hanibal Square Heritage Center