Oakland Car Stroll

“Long ago” Winter Garden had a downtown car show every few months; the last event was just before covid hit in January 2020 and with downtown still with lots of outdoor seating rather than parking spaces, there’s no longer space for that type of car show.

There have been some car shows in Hamlin but they’re not really the same (mostly more modern cars in a parking lot); there’s also a regular car show at the Margaritaville Resort on US 192 but it’s far enough that we’ve only been twice.

But today we had a nearby “car stroll under the oaks” in Oakland sponsored by Shannon Till; the cars were parked along the West Orange Trail and on the grass (there’s not a lot of space in Oakland!) and we enjoyed our “stroll” …

Modern Day Renaissance: The Winter Garden Story

The Winter Garden Heritage Foundation had an interesting exhibit concerning the decline and recovery of downtown Winter Garden, and I took photos to remember before the exhibit ended …

A gradual decline that began in the late 196os has been replaced by an ever-evolving center of commerce, culture, and enter-tainment … Beginning approximately thirty years ago the dreams of these visionaries coagulated into a variety of movements and projects that became enduring cornerstones of the community … entailed. Looking into the past at those who began the revitalization of our beloved city …

Winter Garden experienced a gradual decline throughout the middle of the twentieth century before reaching its lowest point at the end of the 1980s. By then, multiple cataclysmic freezes had decimated much of the citrus industry upon which the town’s economy greatly relied. In 1989, the temperatures plummeted so low that it even snowed, spelling certain death for citrus trees. Empty storefronts, abandoned railroad tracks, and bumpy asphalt roads characterized the Downtown Historic District, and only a shadow of the life and energy of times past remained. For example, during the entire year of 1991 not one construction permit was issued in the area. Not many people were coming to spend their time or money in Winter Garden; aside from a handful of businesses, downtown was not a destination

Since its construction in 1927, the Edgewater Hotel has been the tallest building along Plant Street. Despite its imposing presence it spent much of that time in an abandoned state … the Edgewater shut its doors in the late 1960s … When the Plant Street revival movement took hold, a debate began on whether to restore or demolish the hotel … From 1935 through 1963, the Garden Theater stood as one of the only constant sources of entertainment in Winter Garden. Often, young moviegoers sat in the theater for hours, watching a feature multiple times, “laughing and hollering with the crowd as it grew throughout the evening” according to a local resident. This lasted until the popularity of television reduced moviegoing audiences … the Garden Theater finally reopened in 2008 … One of the oldest establishments … is Tony’s Liquors … throughout its 109-year history the venerable building has served many different functions: hotel, garage, wartime USO club, furniture store, and liquor store … The oldest building in Winter Garden’s Downtown Historic District sits on the southwestern corner of Main and Plant Streets …””Since its construction in 1927, the Edgewater Hotel has been the tallest building along Plant Street. Despite its imposing presence it spent much of that time in an abandoned state … the Edgewater shut its doors in the late 1960s … When the Plant Street revival movement took hold, a debate began on whether to restore or demolish the hotel … From 1935 through 1963, the Garden Theater stood as one of the only constant sources of entertainment in Winter Garden. Often, young moviegoers sat in the theater for hours, watching a feature multiple times, “laughing and hollering with the crowd as it grew throughout the evening” according to a local resident. This lasted until the popularity of television reduced moviegoing audiences … the Garden Theater finally reopened in 2008 … One of the oldest establishments … is Tony’s Liquors … throughout its 109-year history the venerable building has served many different functions: hotel, garage, wartime USO club, furniture store, and liquor store … The oldest building in Winter Garden’s Downtown Historic District sits on the southwestern corner of Main and Plant Streets …

“Jack L. Quesinberry (1931-2017) served 16 ½ years as mayor of Winter Garden (1991-2008), the longest-serving mayor in the city’s history at that time … Jack’s leadership would steer the city’s revitalization for almost two decades … In 2008, the City of Winter Garden commissioned a new home for itself at 300 West Plant Street. The architect designed the building in a retro, art-deco style to provide some consistency with the atmosphere of the historic district …

And some more historic photos …