The Newest Monument In Winter Park Sits Two Blocks West Of Park Avenue

"That number, that's mine."

Fairolyn Livingston is pointing at a house on a mural, the number 800 painted next to the word "family." She was born a block away from where she's standing, and the mural marks the spot on West New England Avenue where she grew up. Her story, along with dozens of others gathered by neighbors over two decades, is why the most recently dedicated piece of public art in Winter Park isn't near the lakefront at all. It's two blocks west of Park Avenue, in Hannibal Square, and it's barely two years old.

Most people who've lived in Winter Park for a while think of that history as settled, something you'd find in a museum case rather than something still being built. That assumption is wrong on two counts. The city's newest monument was unveiled in August 2024. The neighborhood's signature art exhibit added new work as recently as this past fall and winter. This isn't a plaque you glance at once. It's an active project with a staff, a calendar, and a family name still attached to a house number.

A Monument Two Years Old, Next To A Community Center

The Shady Park Pioneer Memorial went up beside the Winter Park Community Center on New England Avenue, on the former site of Hannibal Square Elementary School, the first public school for Black children in the area, founded in 1883. City leaders and residents gathered for the dedication on August 3, 2024, according to Winter Park Voice's coverage, which described four bronze busts backed by a small pyramid topped with a sculpture of elephant tusks, a symbol the artist tied to the neighborhood's name.

The four figures are Mary Lee DePugh, founder of the Ideal Woman's Club, Gus Henderson, founder of the newspaper The Advocate, and Frank R. Israel and Walter B. Simpson, the first two Black men elected to Winter Park's town council. Sculptor George Gadson explained the tusks directly: "The elephants represent symbols of strength, wisdom, and longevity." The project had been in motion since 2022, when the city decided to remove a splash pad that once occupied the site and asked residents what should take its place instead.

The Mosaic That Took 500 Hands To Build

A few steps away sits a different kind of monument, one made of tile rather than bronze. The Community Pride in Hannibal Square mosaic was created by more than 500 students, artists, and volunteers drawn from Killarney Elementary School, Dommerich Elementary School, Crealdé School of Art, and the Winter Park Community Center, funded in part by the Golden Rule Foundation and the Elizabeth Morse Genius Foundation. It depicts a single afternoon in 1887 that determined whether Hannibal Square would be part of Winter Park at all.

The first vote on incorporation, held that September, failed to reach a quorum. A local businessman named J.C. Stovin had convinced many Black residents that incorporation was cover for higher taxes, and turnout stayed low. Henderson and his neighbors spent the following weeks going door to door. On October 12, 1887, he led a march of Black registered voters across the railroad tracks to cast ballots at Ergood's Drugstore, according to the Orange County Library System's history of the center. Quorum was met. Winter Park became a town, with Hannibal Square inside its borders, and Simpson and Israel took seats on the council, the only two Black men ever elected to it.

That last detail matters. Six years later, white residents petitioned the Florida Legislature to overturn the results, and the legislature agreed, removing Hannibal Square from the town limits entirely. The mural and the memorial both exist because a handful of people decided that story shouldn't disappear with the boundary line.

What You Actually See When You Walk In

Walk through the door at 642 West New England Avenue and you're inside the Hannibal Square Heritage Center, run by Crealdé School of Art since 2007. The permanent Heritage Collection now holds more than 200 framed photographs and oral histories tracing life in the neighborhood back to the 1880s, gathered from residents who volunteered their own family albums during a series of Community Heritage Days that started in 2002.

Admission is free. Hours run Tuesday through Thursday from noon to 4 p.m., Friday from noon to 5 p.m., and Saturday from 10 a.m. to 5 p.m. Orange County Library System cardholders can also check out passes to the center, a detail worth knowing if you'd rather plan a visit around a library trip than pay full attention to a schedule. Visitors get a docent-led walk through the collection, guided by staff who grew up hearing these stories secondhand or, in Livingston's case, lived them firsthand.

A Living Project, Not A Closed Exhibit

The center's signature exhibition isn't static either. The Sage Project, a collaborative effort launched in 2007 and first shown in 2012, reached its third phase last fall, adding new portraits to a collection of 42 environmental photographs taken between 2012 and 2025. Phase III opened on September 19, 2025, and closed in late January, thirteen years into a project that keeps building rather than closing the book.

Programming keeps moving too. In recent Juneteenth programming, center manager Jasmine Harris framed a community quilting workshop around textiles as tools of "resistance and reclamation." A quilting circle, led by center historian and docent Mary Daniels, still gathers once a month in the same room. Younger visitors get their own recurring event, a free children's storytelling hour built around a character named Miss Minnie the Mule, who reportedly makes an appearance at the Saturday farmers market too.

Walk It Yourself

Crealdé offers a guided walking tour that stays within a mile loop, passing sites like Mount Moriah Missionary Baptist Church, the Masonic Lodge built in 1927, and the Welbourne Day Care and Nursery, founded the same year. Comfortable shoes and weather protection are worth bringing, since the whole route is outdoors.

If you already spend Saturday mornings at the farmers market, you're closer than you might think. That market runs out of the old train depot at 200 West New England Avenue, on the same street as the Heritage Center, just a few blocks farther west. It's an easy pairing: produce and coffee first, then a walk down the block into a history that most of Winter Park drives past without knowing it's there.

None of this is filed away. The memorial is two years old. The mosaic's story keeps getting retold by staff who learned it from the people who lived it. The exhibit changes. The quilting circle meets again next month. Hannibal Square isn't a chapter Winter Park finished writing. It's one the city is still adding to, a few blocks west of the avenue everyone already knows.

If you're weighing a move within Winter Park, or just want a clearer sense of what makes different pockets of the city distinct from one another, Denise Beserock can walk you through the neighborhoods with the same attention to detail. Let's Connect.