The founding citizens of Winter Park who moved from upper-class Northeastern communities needed housing accommodations for both themselves and their maids, servants, and other “help.” To support a vibrant service industry for these elite newcomers, Hannibal Square (a set of small plots to the west side of the railroad tracks) was built into the urban planning of Winter Park from the very beginning, making it one of the first planned communities for African American workers in Florida. (1) Despite its location next to the predominately white and wealthy Rollins College, Hannibal Square embodied the typical Southern experience for African Americans, who lived and worked in segregation, and often in a state of near poverty.
For employment African Americans at the turn of the century in Winter park held mostly low-income agricultural jobs, bolstering the then-vibrant local citrus industry in Florida, or service industry positions available at local tourist spots including the Winter Park Country Club and the Seminole Hotel. (2) After the Great Freeze in 1895 and the subsequent ruin of most of Florida’s citrus crops, the leisure and tourist industry became an even more critical employment field for people of color in central Florida; childcare, cleaning, food service, and even golf caddying were common professions for Hannibal Square residents at the turn of the century. (3) This trend seemed to continue into the 20th century as well. According to my classmate’s research, most African Americans working at Rollins College in the 1930s were from the Hannibal Square area and had employment in manual labor positions on the grounds and custodial crews.
- Jim Norris, Claire Strom, Danielle Johnson, and Sydney Marshall, Images of America: Winter Park (Charleston: Arcadia Publishing, 2015), back cover.
- “Office of Old Seminole Hotel,” photograph from Seminole Hotel (old) folder. Winter Park, FL c1886, Rollins College Archives and Special Collections.
- “Winter Park Country Club Caddies,” photograph from “African Americans” folder. Winter Park, FL c1900, Rollins College Archives and Special Collections.
— Erin McFee