Things to Do in Winter Garden, Florida

There are plenty of things to do in Winter Garden, Florida—places to see, food to eat, stores to shop at. And the kids can join in on the fun too! If you’re looking for places to visit near Orlando, you won’t be disappointed with what Winter Garden has to offer.

brick building on Main Street in Winter Garden, Florida

Located 14 miles west of Orlando, Winter Garden has a population of 46,051. It’s a small city with a variety of activities to enjoy! As a real estate agent, I highly recommend this area to my clients that are looking to move to Orlando. Central Florida has a lot to offer, and Winter Garden is one of the best!

Fountain in the middle of Main Street in Winter Garden, Florida

Fun Things to Do in Winter Garden, Florida

Activities include shopping, a theater, two museums, and outdoor recreation.

Farmers’ Market

One of the best farmers’ markets in the state of Florida! You can check out what’s for sale every Saturday from 8am to 1pm. It’s located at the Downtown Pavillion on Tremaine Street.

Hiking and Biking Trails

There are plenty of opportunities for outdoor recreation. The West Orange Trail is a popular landmark. This is a 22-mile, mix-use trail that’s ideal for walking, jogging, biking, and skating. It also connects residents to the downtown area, so getting around without a car is a breeze.

a bridge along West Orange Trail in Winter Garden, Florida


Another outdoor park with a trail is Tucker Ranch. There is a playground for your kids and trails to explore that are dog friendly.

Not far from downtown Winter Garden is the Oakland Nature Preserve. There is lots of wildlife to enjoy here.

sign that reads Oakland Nature Preserve at the entrance near Winter Garden, Florida

In addition, Winter Garden boasts several neighborhood parks. Veterans Memorial Park contains basketball courts, a picnic area with grills, softball fields, multipurpose fields, tennis courts, a volleyball court, and a playground. Newton Park features boating, fishing, and picnic areas.

Additional parks include Braddock Park, Maple Street Park, Zander’s Park, Dr. Bradford Memorial Park, Chapin Station Neighborhood Park, and Warrior Park.


SoBo Art Gallery: If you enjoy art, then you will love this. New exhibit every month!

Where to Shop

There are quite a few places to shop, none of which will disappoint. The Historic Downtown District is the place to be.

Street View of Plant Street Market in Winter Garden, Florida

Ms. Bee’s Popcorn & Candy Shoppe: Anyone in town will recommend Ms. Bee’s gourmet popcorn! Check their Facebook page for updates as their shop is currently under construction.

The Sacred Olive: A speciality store for olive oils, vinegars, and bread dippings!

Adjectives Market: There are lots of vintage furniture pieces and collectibles here.

The Boutique on Plant: Boutique shop with plenty of clothes and jewelry!

Where to Eat

Urban Flats: Food, wine and spirits in a sports bar setting.

MoonCricket Grille: In this chill atmosphere, you can enjoy burgers and other bar food. On certain nights of the week, there is live music. Plus a big beer selection!

Winter Garden Pizza Company: When you’re craving pizza, this is the place to go. They also serve calzones, pasta and sandwiches.

The Deli Downtown: As the name suggests, you can order all sorts of deli sandwiches.

Thai Blossom Restaurant: If you’re craving Asian food, you will love this establishment. They are serving all sorts of popular Thai dishes including curry and noodles.

Plant Street Market

This place has so much to offer! It has at least 20 vendors in an old brick building that was refurbished to be the place to hang out 7 days a week.

Crooked Can Brewing Company: If craft beer is your thing, then this is the local brewery in town that you need to check out! All sorts of food is located right next door in the adjacent Plant Street Market.

the front doors of Plant Street Market

There is plenty of food to eat at Plant Street Market. Here are a few options:

  • Mac’d Out
  • Jodo Sushi
  • Ceviche Mix
  • This Little Piggy
  • Morthan Cheese
  • Sir Benji’s Donuts
  • Michael’s Ali Coal Fired Pizza
  • Paleteria Original Handcrafted Popsicles
Bar area inside of Plant Street Market

If you’re interested in relocating to Winter Garden, Florida, you can contact me here.

Nicole Mickle

I've lived, worked, and played in Orlando my entire life. Let's make the most out of your Florida lifestyle! I'm here to help you take overwhelming interior design options and simplify them room by room.

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