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.

On October 12, 1887, young businessman and newspaper publisher Gus Henderson violated curfew to lead a march of African American registered voters across the railroad tracks to Ergood’s Drugstore. 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 professional standing among its African American residents.

For over one hundred years, the intersection of New England and Pennsylvania Avenues was the heart of the shopping and entertainment district for the local African American community. Today’s Hannibal Square merchants enjoy the neighborhood feeling that comes from being part of an existing community of residences, churches, community centers, playgrounds, train access, and beautiful parks.

Although time has changed the character of the neighborhood, the merchants work hard to preserve the village ambience, and to celebrate and support what is remaining of the historic neighborhood. In 2007, the City of Winter Park and Crealdé School of Art opened the Hannibal Square Heritage Center at the west end of the shopping district. Through a unique, award-winning exhibition of historic photographs and oral histories The Hannibal Square Heritage Center pays tribute to the past, present and future contributions of Winter Park’s historic African American community. You will find that Hannibal Square is not just another mall—but a thriving historic community with something for everyone.