Good Towns: Winter Garden, Florida

Joe Williams spots a couple of strangers exploring near his office and stops them with a statement: “You must be important because you’re carrying a legal pad and a camera.”

Truer words were never spoken. The Doing More Today team has landed in our latest Good Town, Winter Garden, Florida, to explore this small enclave just 14 miles from Central Florida’s best-known destination, Disney World.

And a chance encounter has led to Williams, an engineer, real-estate investor and unofficial historian.

“People in Winter Garden smile and make you happy,” Williams explained. “I came here in 1977, when it was just an old grove town and not much else. Really, it was a hole in the wall. And look at it now.”

The first thing you notice, beyond a lot of happy, smiling people, is a downtown that’s hip and vibrant, yet a throwback to a quainter, gentler era. The West Orange Trail, a 22-mile greenway, cuts through the middle of Plant Street, the hub of this re-energized area that’s packed with visitors moving leisurely from shop to restaurant to the trail from dawn to dusk – and beyond.

“As long as you have retail, you have a great nighttime experience,” Williams said. “When I got here, the roads behind us were clay and the buildings were industrial. Now, everyone works together upgrading and creating an experience that’s like no other.”

Quirky and Cool

By 8 a.m., Plant Street is abuzz with activity. Young moms with strollers move up and down the sidewalks. Joggers head down the West Orange Trail. Young professionals, dressed in business casual to combat the muggy heat, head to the office.

But the busiest bees wear shirts identifying their role with the city’s parks and recreation department as they sweep the streets and painstakingly manicure the luscious landscaping that sets downtown Winter Garden apart. As one employee pressure washes a fountain, creating a stunning rainbow in the wake, another trims hedges with the attention of an artist while a co-worker digs in the dirt preparing a new flower bed.

Taking it all in, Krysta Tootle sips a cappuccino at a table next to her 3-year-old daughter Charlotte as 1-year-old twins Austin and Bryson smile from a double stroller. It’s a pleasant diversion before heading to swimming lessons.

Tootle grew up in South Florida and moved with her husband to nearby Clermont three years ago – just in time for everything to shut down due to the pandemic.

“It was a tough time because you had to adapt to a new environment that made it harder to make new friends,” Tootle said. “But we eventually did because it’s an easy place to meet nice, new people. And the best part, there’s just so much to do and see – downtown Winter Garden, the Farmer’s Market, Plant Street Market. It’s safe and welcoming.”

Back in his office, Joe Williams tells more of his story.

Williams was working as a surveyor in Washington, D.C., when, at 17, he decided to try his luck in Central Florida.

“After the war, the town was hopping,” he said. “Railroads came through town to get the oranges and Winter Garden was full of grovers.”

The commerce attracted people. At one point, Winter Garden seemingly had a movie house at every corner, beginning with the “Upstairs Theater” on the corner of Plant and Main. The Movie Hut and Winter Garden Theaters I and II followed, as well as the Gem and the Starlite – the latter a state-of-the-art drive-in that opened in 1949 and accommodated 250 cars (with an admission price of 35 cents).

Today, the Garden Theatre lures visitors from across the region with professional stage productions that give downtown its artistic vibe.

But, over the years, the economics and demographics changed. By the time Williams arrived, Winter Garden was dying.

Then, the big mouse kingdom to the east opened, tourists flocked and Winter Garden, like all the other small towns surrounding Orlando, began to cash in on the influx of visitors from across the globe. But few did it better than Winter Garden, creating an idyllic focal point that peels away layers of stress even as the temps rise.

Williams loves the historical side of the town, as well as the quirky. His office is filled with miniature trains, some that run from one room to the next. And at home, out towards nearby Oakland, he’s created a masterpiece that locals love to drive by and gawk at – especially at Halloween. The two-story gothic house has an Addams Family feel, adorned with unusual embellishments out front including a cannon, an old fire truck and a vintage sedan.

Watch Out for the Gators

You can get a feel for old Florida by heading to the edge of Winter Garden.

At the Oakland Nature Preserve, you can hike through a 150-acre natural area on the south end of Lake Apopka that offers sightings of birds and other Florida critters along a relaxing trail. Lake Apopka was the original draw to the area, luring fishermen and farmers, but the state’s second-largest lake was nearly destroyed by the release of fertilizers and sewage into the body of water decades ago.

Now, the lake is coming back to life, and a trip to the preserve provides a road map for ecotourists on the impact humans have on nature.

A few miles to the east, you can take the Wildlife Drive Fridays through Sundays. It’s a meandering hour-long drive along the east side of Lake Apopka that can take much longer thanks to the 10-mph speed limit and people constantly stopping to take photos. Actually, the longer it takes the better, as the 200 acres of wetlands offer a surprise at every turn.

Just heed the warning signs – especially the one telling you to watch your step during alligator mating season. If you are comfortable with your surroundings, and confident that you are safely away from the most amorous reptiles, look skyward. On Christmas Day 1988, bird watchers counted a record 174 species, from herons and egrets to flycatchers and warblers.

‘I Can’t Imagine Living Anywhere Else’

As dusk approaches, downtown Winter Garden is full of wanderers soaking the scene in. The outdoor patios of Plant Street Market are packed with people enjoying local cuisine and craft brews from Crooked Can Brewing Company available inside the artisan shops. If you need a pick-me-up, you can inhale a whiff of pure O2 from one of the vendors.

Down the street, traffic flows in and out of Wheelworks, a hip Orlando bike shop that lures commuters and athletes that regularly trek the West Orange Trail.

Chet and Hiede Carroll moved back home after success in San Diego in the corporate world, intending to retire from the hustle and bustle. Within a year, the retiree life got boring, so they plugged back in with jobs – Hiede as an executive accountant in the hotel industry, Chet helping buyers find the right bike at Wheelworks.

Chet’s co-worker, Felipe Guagliardo, used to run helicopter tours in Orlando. Since returning to Winter Garden, he’s cut his commute down by two thirds, to 15 minutes.

“Now I do something that’s more geared to my hobby, riding bikes, and I’m working in the community I grew up in,” Guagliardo said. “I’ve seen Winter Garden go from sleepy to woken up. It started with the Plant Street Market and exploded from there.”

Anchoring downtown is the Historic Edgewater Hotel. Originally an enclave for visiting fishermen, it opened as a high-tech bed-and-breakfast nearly a century ago. Now, it includes restaurants and an ice cream shop, as well as rooms and space that lure weddings, anniversaries and family reunions to the rich, wood paneling, antique fixtures and the original 1926 Otis elevator.

A few blocks away, at the SOBO Art Gallery, Sandra Baier fills her days perusing local art, taking classes and showing off the local talent to visitors.

“We moved here a year and a half ago from New Hampshire, and it was a culture shock,” Baier said. “Now, we’ve adjusted. I love the weather and the people are super friendly. I can’t imagine living anywhere else.”