17 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. 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 offers.

Located 14 miles west of downtown Orlando, Winter Garden has a population of 46,051. It’s a small city with a variety of activities to enjoy! This is a great place to live if you want to relocate to Florida. Central Florida has a lot to offer, and Winter Garden is one of the best!

brick building on Main Street in Winter Garden, Florida

Activities include shopping, a theater, two museums, and beautiful parks with plenty of wildlife. Whether you’re looking for a day of relaxation or some fun in the sun, there’s something to do in Winter Garden.

1) Visit the Winter Garden Farmers Market

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

2) Go biking on the West Orange Trail

Address: 1064 Tildenville School Rd, Winter Garden, FL 34787

There are plenty of opportunities for outdoor recreation. The West Orange Trail is a popular landmark.

This 22-mile, the mixed-use trail is ideal for walking, jogging, biking, and skating. It also connects residents to downtown, so getting around without a car is a breeze.

3) Visit a beautiful park

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

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

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

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.

4) Visit the SOBO Art Gallery

Address: 127 S Boyd St, Winter Garden, FL 34787

If you enjoy art, then you will love SoBo Art Gallery. Check their schedule to see what their upcoming exhibitions are.

5) Explore the Historic Downtown District

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

  • Adjectives Market: There are lots of vintage furniture pieces and collectibles here.
  • The Boutique on Plant: Boutique shop with plenty of clothes and jewelry!
  • Urban on Plant Kitchen & Bar: Food, wine, and spirits in a sports bar.
  • MoonCricket Grille: You can enjoy burgers and other bar food in this chill atmosphere. On certain nights of the week, there is live music. Plus, an extensive beer selection!
  • Winter Garden Pizza Company: This is the place to go when you’re craving pizza. 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: You will love this establishment if you’re craving Asian food. They serve all sorts of popular Thai dishes, including curry and noodles.

6) Eat gourmet popcorn and sweets

Address: 13900 County Rd 455 Suite 115, Clermont, FL 34711

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 – their new location is now in nearby Clermont.

7) Explore Plant Street Market

Address: 426 W Plant St, Winter Garden, FL 34787

the front doors of 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 seven days a week. 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

8) Have a beer at Crooked Can Brewing Company

Address: 426 W Plant St, Winter Garden, FL 34787

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.

9) See a show at the Garden Theatre

Address: 160 W Plant St, Winter Garden, FL 34787

There is so much history at the Garden Theatre, dating back to 1935. Now you can watch movies here, live theatrical productions, and comedy shows. This community-based theater allows local actors to audition for their live performances.

10) Watch the sunset at Newton Park

Address: 31 W Garden Ave, Winter Garden, FL 34787

Newton Park is an excellent park with lakefront views, and you can watch the most amazing sunsets here! The wildlife is beautiful. There are tons of birds as well as alligators and fish. You can enjoy a walk along the edge of the lake or down one of the docks.

11) Hang out at Hagan O’Reilly’s Irish Pub

Address: 16112 Marsh Rd, Winter Garden, FL 34787

The Hagan O’Reilly’s Irish Pub has a great atmosphere with live music and another bar outdoors. The shepherd’s pie and corned beef and cabbage are both delicious. The bar had a good selection of drinks, including Guinness and cider. Prices are reasonable too.

12) Have a wine night at The Attic Door

Address: 28 W Plant St, Winter Garden, FL 34787

Order some sangria at The Attic Door! Photo Credit

Winter Garden has its own wine bar, which is fantastic! The Attic Door has a fun atmosphere with live music, comfortable couches, and a vast menu that includes appetizers and craft beers local to Florida.

13) Order a latte at Axum Coffee

Address: 146 W Plant St STE 110, Winter Garden, FL 34787

Axum Coffee is probably one of the coziest coffee shops you will ever visit! Try the Charcoal Mocha – it will not disappoint you!

14) Order a pastry at Rosallie Le French Cafe

Address: 141 W Plant St, Winter Garden, FL 34787

Rosallie is a lovely little french cafe with a cute interior and a menu you’ll love. The pastries and lattes are the best! For something unique, order the honey and lavender latte or rose mocha. They serve brunch all day so you can order a quiche for a light meal.

15) Watch a game at Miller’s Ale House

Address: 12175 W Colonial Dr, Winter Garden, FL 34787

Miller’s Ale House is a popular sports pub. The menu has an excellent selection of beers, wings, burgers, and sandwiches. It’s just a laidback atmosphere to hang out in after work or watch your favorite game.

16) Escape Goat

Address: 12175 W Colonial Dr, Winter Garden, FL 34787

Escape Goat is a local escape room, so there’s no need to drive to International Drive or downtown Orlando to experience this! It’s fun to hang out with your friends and build teamwork skills together. The experiences include A Fisherman’s Tale, Operation Treehouse, Area 51, and The Quest.

17) Go shopping at Winter Garden Village

Address: 3041 Daniels Road, Winter Garden, FL 34787

The Winter Garden Village is a shopping mall with lots of trendy shops for you to enjoy. It has dozens of retailers, including Lane Bryant, Old Navy, Victoria’s Secret, and Forever 21. If you get hungry, you can dine at Chick-fil-A, Panera Bread, Red Robin, or Panda Express – to name a few! Overall, it’s a nice outdoor shopping complex that will meet your needs.

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