12 December 2021

Winter Park Mall, Winter Park, FL

A dead mall

One of the most magical places I’ve ever known happens to be located amongst the swamps and endless lakes of central Florida.  There were tree lined roads, buildings right out of a Norman Rockwell painting, plenty of fun animals to play with, and it all surrounded an amazing main street full of shops, restaurants and parks.  I’m speaking, of course, about the Orlando suburb of Winter Park, Florida.  The close-in little village with its Park Avenue and tree lined neighborhood thoroughfares, was home to two of the most magical people any kid could know- their grandparents.


1- The mall interior just after opening (Source); 2- The twin towers at the mall entrance (Source); 3- The original fountain at center court (Source); 
4- Another view of the mall's central area (Source)

1985 was the year we lived with our grandparents while my Navy father was away at training and the rest of us were transitioning to a new home in Virginia from Hawai’i.  And my father’s childhood home was triangulated in the middle of three early Orlando shopping classics- Colonial Plaza, OrlandoFashion Square and the Winter Park Mall.


More old school interior shots of groovy Winter Park Mall (Source) (Source)

Even though we lived in Winter Park, we spent relatively little time at its eponymous shopping complex.  Orlando Fashion square was the big super-regional that seemed to have everything while Colonial Plaza had a huge Jordan Marsh, one of my grandmother’s favorite stores (along with Maison Blanche.)  So it just seemed logical that we would head south from our post World War II rancher on Dunraven Drive to Colonial Drive to our most visited places.  For the longest time, since Winter Park Mall was located so close to our church on Park Avenue, the only time I ever got a look at the mall was when driving by for a post worship brunch on some nameless diner on Orlando Avenue.


Winter Park Mall's layout at its opening.

From our place on the busy highway as we passed, Winter Park Mall looked basic enough, with an Ivey’s bookending the north while Penny’s anchored the south.  What caught my eye the most, however, was the main entranceway.  It was flanked by two tall, narrow towers, or spires, if you will.  The rest of the mall was a drab monolith with a low slung roof and as flat as the Florida peninsula itself.  But these two features absolutely fascinated me.


Old school post card of the mall. (Source)

That’s why when, one afternoon, my grandmother announced that she intended to make a trip out to the Winter Park Mall, any attempt to hide my excitement was in vain.  My aunt, who was still in high school at the time, felt a bit different.  But there’s nothing there, she said.  I hate the Winter Park Mall.  My grandmother, a very gentle yet assertive human being barely standing over five feet tall simply answered, I like the winter Park Mall. And off we went.

An old article about the mall (Source)

 Finally… I thought as I walked between those two towers for the first time.  We walked through the main entrance doors and immediately, the first sense to get hit was smell.  It was a bit musty and drab, and showed its age even more than the older Colonial Plaza.  But it was a new experience, and I was taking it all in.  I remember the tall, pink-ish and beige-ish walls reaching up to a flat conventional ceiling with small skylights allowing the sun to peak through its parallel slats.  I remember the “inverted mushroom” water feature in center court and just a few feet away, what I thought was their food court.  It was simply a few food kiosks gathered together with latticework being their most innovative design feature.  It was...  Different. 

Management around a mall map and the original fountain. (Source)

Whenever going to a new mall, my first destination, and this is still something I do today, is the directory.  Winter Park was your basic, early generation, single tiered dumbbell shaped facility with around 40 or so stores.  I searched all around that dadgum directory to see if I could find what was usually my second destination- the information booth.  Here was where I was usually able to get my hands on my most prized possession- a mallmanac.  Alas, no matter how much I looked up and down the main concourse, with nary a corner being outside of ninety degrees, I could not find one.  No booth, no mallmanac.  I was crushed.


Winter Park Mall's layout in the late eighties.

A quick trip to the Woolworth diner for a grilled cheese sandwich did cheer me up a bit, but it always seemed that if I didn’t walk out with at least one of those shiny brochures; I may as well have stayed home.  So, I tried to imprint that place as well as I could into my ten year old brain, which was already full of airplanes and anime.  Which was a good thing.  By the mid to late nineties, Winter Park Mall was gone.

Winter Park Mall shortly before its closing. (Source)

Winter Park Mall opened in 1964 as the Orlando area's first enclosed shopping mall.  The original anchors were Ivey's and JCPenney.  In the years after the facility survived the first fire at an enclosed shopping mall in 1969, it performed well enough during the eighties but started its major decline in the nineties. Even as Dillard's replaced Ivey's, it never seemed to be a hit in the affluent suburb.  In a reverse of retail trends seen nationwide, the town's original shopping district on Park Avenue not only survived, but flourished.  As the mall faltered, the neighboring district became known as the downtown that killed the mall.

1- Winter Park Mall from above; 2- The Winter Park Village redevelopment from above. (Source)

In 1998, all but the Dillard's anchor was demolished to make way for Winter Park Village, one of the country's first major transformations from a single use mall to mixed-use commercial, retail and living space.  It has proven to be a success as the new center compliments, rather than competes with, nearby Park Avenue.

Winter Park Village Pamphlet ca. 2002.  View the full PDF version here.

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