The Winter Park Mall, known today as Winter Park Village, opened in 1964 as the Orlando area’s first enclosed shopping mall. In the decades since, it’s evolved alongside the city it calls home — gradually phasing out original tenants and welcoming new ones, and ultimately transforming into an outdoor mall in 1999. With its latest renovation, Winter Park Village embraces the pioneering spirit that willed the shopping center into existence nearly 60 years ago to yet again reimagine the way shoppers, diners, and visitors will interact with the space.

For Dix.Hite, Winter Park Village’s evolution also bridges past and present. Firm Principal David Hoppes served as lead landscape architect on Winter Park Village’s 2022 revitalization, and team member and industry veteran Tom McMacken served as project manager on the 1999 remodel. To understand what went into each of these undertakings and to better chart our shared history, we sat down for in-depth conversations with Tom and David.

Early Days 

 “The original Winter Park Village (the Winter Park Mall) was your typical ‘60s-era mall,” Tom remembers, “with your interior shopping center surrounded by a sea of parking.” Founding tenants included anchors like the Charlotte-based Ivey’s (which was later bought out by Dillard’s,) and J.C. Penney — at the time, the second-largest location in the States. This 1960s ideal remained as tenants cycled in and out. But with the increasing popularity of the nearby Park Avenue shopping district, Winter Park Village’s attendance waned. With redevelopment seeming like the only way to breathe new life into the property, much of the mall was razed in 1998 to make way for an entirely new concept.

A New Mall for the New Millennium  

 Witnessing the popularity of Park Avenue, the redevelopment firm CASTO saw a way for Winter Park Village to have a memorable second act. As Tom states: “We effectively took the original mall and exploded it — stores went on the outside, with footpaths and parking in the middle.” This idea was revolutionary, and not entirely popular, as trading air-conditioned corridors for the unbridled Florida heat seemed counterintuitive to some shoppers (and would-be tenants). But with Winter Park Village’s official reopening in 1999, it seemed as though a new era of the mall had arrived. “If you look at a lot of Florida’s major modern shopping centers, they’re outdoor, and I think the revamped Winter Park Village was the tip of that spear.”  

Balancing Parking and Pedestrian Spaces 

 If you’ve visited Winter Park Village in recent years, you’ll have likely spent a few minutes hunting for a parking spot. That scarcity is by design. “Most designers and planners design with the Christmas Eve crowd in mind. We designed around every day,” Tom remembers. But even with strategically limited available parking, cars still appeared to be winning the game of tug of war. So, with Winter Park Village’s most recent reimagining, guaranteeing equal footing for pedestrians and vehicles was a high priority. As David Hoppes puts it, “The goal was to make drivers feel just uncomfortable enough — so they drive slower and react differently.”  

In this case, leveling the playing field was more than a figure of speech, with Gay Road (the Village’s “Main Street”) raising a full 18 inches in the new design to form a seamless connection with the sidewalk. Bollards were implemented for an added layer of protection — and eliminating the area’s notoriously high curbs helped ensure ADA compliance while creating a more walkable and open environment for every visitor.

Experience-Driven Design 

Revitalizing Winter Park Village was a team effort through and through. Dix.Hite partnered with a comprehensive team of firms to define primary objectives for the shopping and entertainment complex. Retail consultants were also brought into the fold, ensuring the next generation of tenants spoke to the goals of the updated design. The determination was made that each space should either allure, enchant, amuse, or offer a place to unwind, descriptors which helped guide Dix.Hite’s design process. “There were existing spaces where four specific businesses suffered,” David notes, “so we created an inviting breezeway to add to the allure of this area.” The existing park, known for its oversized chess board (“don’t worry, it’s making a comeback”) also got a second, experience-driven life. “We wanted the park to feel like it extends from building face to building face, so when visitors leave dinner they can glide to a movie — feeling as though they haven’t ever left the park.” Enchanting, indeed.

Embracing Challenges 

Still, with a suburban retrofit project, unexpected (and expected) challenges are bound to arise. Older structures come with baggage, but an unfortunate casualty of the redesign was the rows of live oaks that lined Winter Park Village’s major thoroughfares. “The original planters were just too small, and they sadly weren’t going to make it.” In their place, Dix.Hite dedicated new trees, “which, 10 years from now, will offer a similar canopy.” Better yet: they’ll be healthy. Through the near-four-year design and construction process, “there were some… tense moments,” David laughs, “but we remained focused on delivering exceptional client service whenever possible.”   

Designing the Future 

When Tom McMacken helped breathe new life into Winter Park Village at the close of the millennium, he said it felt like the beginning of a new era. This newest iteration of Winter Park Village feels similarly vital. Two decades ago, an outdoor mall in the heart of Central Florida seemed revolutionary, even ridiculous to some. But in time, the design proved to be prophetic. David feels that our work revitalizing Winter Park Village may be the starting gun — once again signaling to other developers, property owners, and place makers that it's time to embrace change.

“This experience will be unfamiliar to many. But I think once they visit the new Winter Park Village, they’ll wonder why more of their favorite shopping centers aren’t like this.”