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Best Things To Do in Winter Garden

In the 1990s, I spent a few semesters at UCF. I wish I’d stayed longer, but that’s another story for another time. I lived in on the Orlando campus, but before I moved back to the Gulf Coast, I also lived in Winter Park and Kissimmee.

In all that time, I never visited Winter Garden. If memory serves, I think a lot of us considered it a broken-down place, with not much going for it.

I have no idea if that idea was complete crap, but I do know now — thanks to the urging of my Florida Spectacular podcast co-host and Florida author and artist Rick Kilby — it’s one of my new must-see places when I spend any time at all in Central Florida.

Why do I love Winter Garden? Well, lots of reasons. It’s close to Orlando but feels much calmer than Orlando proper. They have a kick-ass food hall. Trees are everywhere. And, most of all, despite being a stone’s throw from Walt Disney World, well, you’d never know it inside city limits.

Here are my favorite things to do when I visit Winter Garden.

1. Bike Winter Garden. 

   

   The folks at Visit Orlando offered me the opportunity to bike to Winter Garden along the West Orange Trail, and it wouldn’t be first on the list if it didn’t resonate with me. The Trail is shady and peaceful. We started our ride at Killarney Station and rode to Winter Garden (the 22-mile trail actually runs to Apopka), then back again. Along the trail there are plenty of places to stop and rest, rehydrate, hike, and explore.

   Plus, you never know what you’ll see on the trail, like the rhino we spotted (not real, thankfully!).

2. Rest under the trees downtown.

   

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   Once you get to downtown Winter Garden, head to Centennial Plaza, where you can rest a while under a gorgeous arbor. The plaza has a trellis overhead, and the trees at every corner have wound themselves around the arbor,

   The other cool thing here was the fountain. Now, a fountain is a fountain is a fountain — but this one had a nifty nod to the area’s history: mosaic tile art recreating citrus crate packing labels, inlaid along the fountain’s base.

   

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3. Eat at the Plant Street Market.

   

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   I’m a fan of Hunger Street Tacos (that’s their plant-based taco, above) as much as I am the pizza at Michael’s Ali Coal Fired Pizza (pictured below).

   

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   I’m also partial to the sushi (below) and if this feels like a lot, that’s the point of a food hall.  And Plant Street Market does the food hall concept quite well. (Yes, I know they have a Michelin Star for another restaurant, but I haven’t eaten there and can’t tell you if it’s as good as the hype.)

   

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4. Stop and smell the flowers at the pollinator garden.

   

   Along the West Orange Trail, we saw a sign for a pollinator garden, so we stopped to check it out. It had all the colorful and Florida-type plants most pollinator gardens do, but it also had a little something extra: A fairy garden. And this one looked well-used. Whether it’s well used by fairies or kids, well, I can’t say, but I loved seeing this touch of whimsy along the trail.

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   And, finally….

5. Walk the shoreline at Lake Apopka.

   

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   Finally, if you get off the West Orange Trail and drive through Winter Garden, make time to head to Lake Apopka by the marina. Look for the interpretive signage about the lake’s troubled environmental history, but take a moment to appreciate how tides have turned.

   

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   Every important city has love locks; Winter Garden is no exception. And, yes, this love lock bridge is still up-and-coming, but it’s still pretty cool.

   

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   Winter Garden is a great place to visit.

   As you walk the shoreline, you’ll see bridges over the water. Walking these steps and bridges is pretty neat, in a retro-luddite experience kinda way. But then, that’s sort of the entire city’s vibe.

   Please take time to visit Winter Garden. You won’t be sorry you did.

Think Central Florida’s all Disney? Check out how to visit Kissimmee if you don’t love theme parks.