WINTER PARK, Fla. – Walking through Hannibal Square with Fairolyn Livingston is like stepping into a time capsule - one guided by someone who lived the history.
“I was born a block away from here at 800 West New England Avenue,” Livingston says, standing in the Winter Park neighborhood she has called home as a child.
Livingston, who is almost 80 years old, grew up in Hannibal Square, a historically Black community on the west side of Winter Park, just blocks from Park Avenue.
Founded in the late 1800s, Hannibal Square became home to formerly enslaved people, Black laborers, and families who helped build Winter Park during its earliest days.
At a time when African Americans were largely barred from living or owning property in other parts of the city, Hannibal Square emerged as a self-sustaining community during segregation, anchored by churches, schools, and Black-owned businesses. It’s a legacy Livingston says still shapes her sense of pride today.
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“This was the location of my elementary school,” she recalls as we walk near the site. “It’s not the same building, but it’s the footprint of where my elementary school was, where I attended in the 1950s.”
Long before the neighborhood took on its modern look with large homes and high-end shops and restaurants, Livingston remembers Hannibal Square as a place rooted in family and connection.
“On New England Avenue here...that was the business area of the Black community,” she says, noting how much the neighborhood has changed. “Well, it’s gentrified now, so it’s not exactly the way it was.”
Still, she remembers a tightly knit community where education mattered, and churches played a central role in daily life.
“We came from a very cohesive community where education was very important,” Livingston says. “And of course, the churches played a big role.”
Today, Hannibal Square stands as a powerful reminder that Black history is foundational to Winter Park’s story. She says it is history that is often overlooked.
A mural outside the site of Livingston’s former elementary school serves as both a timeline and a testimony. It honors three Black men who helped shape Winter Park in its early years, including Gus Henderson, who founded the city’s first newspaper and served both Black and white communities.
The mural also depicts Walter Simpson and Frank Israel, the first two Black men elected to the Winter Park Town Council. They served from 1887 to 1893 before white residents petitioned the Florida Legislature to overturn the election. The legislature approved the request, removing Hannibal Square from the town limits.
It’s a chapter of history many people were never taught, and one Livingston believes must be preserved.
“And Hannibal Square is going to be here telling the story of how it all came to be,” she says.
One way that the story lives on is through walking tours led by Jasmine Harris, who is the manager of the Hannibal Square Heritage Center. The tours highlight the people who made Hannibal Square and Winter Park what they are today.
“There are pictures donated by family members of loved ones that tell the story of what it was like growing up here,” Harris explains.
From the clothes and the cars to the everyday moments of life, visitors leave with a deeper understanding of the people who shaped this corner of the community.
As for Fairolyn Livingston, her story isn’t just remembered, it’s permanently woven into the neighborhood itself.
Pointing to the mural, Livingston draws our attention to a house marked with the word “family” and the number 800 on it.
“That number,” she says, smiling, “that’s mine.”
The home where she grew up on West New England Avenue is at the center of the mural, firmly marking her place in Hannibal Square.
If you would like to know more about the history of Hannibal Square or have a story you would like to share about the community, reach out to the Hannibal Square Heritage Center by calling 407-539-2680.