15 Best Things To Do In Winter Garden, Florida - Updated 2021

things to do in winter garden florida

Located in Orange County, Winter Garden is just 20 minutes away from Orlando and is full of adventure opportunities, from nature walks to farmer’s markets and a unique street market. Known as being one of the safer places to live in Florida, this little hamlet’s high livability is attributed to its wonderful people. The truest sign that you’re in Florida, however, is Winter Garden’s proximity to Disney, which is just a short drive away. If you’re planning to visit, keep reading to learn about the best things to do in Winter Garden, Florida.

1. Catch a show at Garden Theatre

Editor's Note: Photo taken from the establishment's official social account

Originally constructed in the 1930s, Garden Theatre is a renovated, historic theatre in Winter Garden, Florida. This theatre so far has hosted over 200 events, including music, dance, theatre, and films. Garden Theatre is a non-profit center that also acts as a venue where people can rent for weddings, screenings, and even meetings. It also acts as a primary performing arts center in the entire region of Winter Garden.

Garden Theatre

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

Website: Garden Theatre

Opening hours: Tue - Sat: 12pm - 4pm (closed on Sun & Mon)

2. Walk through SOBO Art Gallery - Winter Garden Art Association

Editor's Note: Photo taken from the establishment's official social account

SOBO Art Gallery in Winter Garden, Florida, is the most popular gallery in the Central Florida region. Several exhibitions have been held throughout the years, where the gallery gets nearly 200+ submissions, and around 50 to 60 art pieces are displayed. This gallery was once a firehouse, which has been renovated into an art center and art gallery that is now run by the Winter Garden Art Association. Monthly art exhibits, art workshops, and several other special events are held at this location.

SOBO Art Gallery - Winter Garden Art Association

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

Website: SOBO Art Gallery - Winter Garden Art Association

Opening hours: Tue - Sat: 10am - 6pm (closed on Sun & Mon)

3. Chill out at The Attic Door

Editor's Note: Photo taken from the establishment's official social account

Posted by The Attic Door on Friday, December 11, 2020

Head to The Attic Door, a cozy wine bar bistro and live music venue when you’re out and about in Winter Garden, Florida. This low-lit wine bar features lounge furniture and eclectic decor. It serves a menu of small, yet tasty dishes that pair well with the drinks offered here. There’s a happy hour that happens daily from 4 pm to 7 pm, and they also host brunch over the weekends, most renowned for its bottomless mimosas.

The Attic Door

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

Website: The Attic Door

Opening hours: Tue - Thu: 4pm - 10pm; Sat: 11am - 11pm; Sun: 11am - 1:30pm (closed on Mon)

4. Grab a drink at Hagan O'Reilly's Irish Pub

Editor's Note: Photo taken from the establishment's official social account

Whiskey lovers, we have a treat for you! Now back in stock, select Pappy VanWinkle premium years! #PappyVanWinkle...

Posted by Hagan O'Reilly's on Thursday, February 25, 2021

An authentic Irish Pub in Winter Garden, Florida, Hagan O'Reilly’s Irish Pub is not a place where you go for just the beers. It’s much more than that. You also get comfort food in a sociable setting, featuring a fireplace, ping-pong table, TVs, and a patio. This is a great place to meet your friends and family. Pair your favorite drinks with comfort food such as mozzarella sticks, bacon cheeseburger, Irish house salad, and grilled chicken wrap, to name a few.

Hagan O'Reilly's Irish Pub

Address: 16112 Marsh Rd, Winter Garden, FL 34787

Website: Hagan O'Reilly’s Irish Pub

Opening hours: 11am - 2pm (daily)

5. Go shopping at the Winter Garden Village

Editor's Note: There's no photo available at the time of writing

An open-air retail center, Winter Garden Village in Winter Garden is a great place to solve all your shopping woes. You can get to shop from over 100 retailers, including Men’s Warehouse, JoAnn Fabrics, and Barnes and Noble, among others. And if you get hungry, you can head to any of the sit-down restaurants, cafes, and dessert stores located within Winter Garden Village. This is truly a one-stop destination for all your shopping needs.

Winter Garden Village

Address: 3251 Daniels Rd, Orlando, FL 34787

Website: Winter Garden Village

Opening hours: 10am - 9pm (daily)

6. Get connected to the earth at Tibet-Butler Nature Preserve

Si quieres estar en contacto con la naturaleza hay varios parques con caminerías a donde puedes ir. Yo fui a...

Posted by Orlando 360vision on Monday, 29 May 2017

Located in Orlando, just twenty-two minutes away from Winter Garden, the Tibet-Butler Nature Preserve showcases trails through pine forests and wetlands. It’s a great place to hike and enjoy the natural scenery and wildlife. The longest trail is 3.6 miles (5.7 km), with shorter loops available, so it’s a good place for beginner hikers. The trails are shaded by pine trees and oak trees.

Don’t miss the butterfly garden, where you’ll be able to see a variety of different butterfly species flitting from flower to flower. Stop by the environmental center for information on the vegetation and wildlife that populate the nature preserve.

Tibet-Butler Nature Preserve

Address: 8777 Winter Garden Vineland Rd, Orlando, FL 32836

Website: Tibet-Butler Nature Preserve

7. Visit the Withers-Maguire House

Rachel and I are going to tour The Withers-Maguire house in town this afternoon!! I have ALWAYS wanted to tour this historic home! We are going with her Girl Scout Troop!❤ Hope I can get some nice pictures!😌

Posted by Renee Richardson Pennell on Saturday, 29 April 2017

Just ten minutes away from Winter Garden, the historic Withers-Maguire House is located in Ocoee. This restored home was originally built in 1888. It was owned by General William T. Withers and then David Maguire before it was purchased by the city, hence the name the Withers-Maguire House. In 1987 it took its rightful place on the National Registry of Historic Buildings. The house offers historic displays from the 1800s and is often used for weddings and special events because of its beautiful architecture.

You can visit every Saturday and Sunday from 2 pm to 4 pm, when it is open to the public and free of charge.

Withers-Maguire House

Address: 16 East Oakland Avenue, Ocoee, FL 34761

Website: Withers-Maguire House

8. Shop at Winter Garden Farmer's Market

Posted by Winter Garden Farmers Market on Tuesday, 9 February 2016

Do you love browsing local, handmade items, antiques, and fresh produce? The Winter Garden Farmer’s Market offers the opportunity to see and purchase all of these items. More than just an outdoor market, the Winter Garden Farmer’s Market also hosts events, offering live music, car shows, and more. Check the website to see what events are planned while you’re in the area. You’ll be sure to catch live music while you’re there, as it is offered every Saturday. You’ll be able to purchase handmade soaps, jewelry, baked goods, herbs, tea, meat and produce, and much more.

The market is open in downtown Winter Garden every Saturday from 9 am to 2 pm.

Winter Garden Farmer's Market

Address: Downtown Winter Garden, FL

Website: Winter Garden Farmer’s Market

9. Take a tour of Crooked Can Brewing Company

Posted by Crooked Can Brewing Company on Wednesday, 18 November 2015

Located right in Winter Garden, Crooked Can Brewing Company is a pet-friendly, family-friendly destination for great food and beer. Most breweries focus on their variety of beer selections, but Crooked Can offers excellent food selections as well, including pizza, sushi, burgers, wings, and a vegan menu.

Crooked Can brews their own varieties, so you’ll be able to sample unique brews. They also offer brewery tours, where you’ll get to sample new flavors and learn about the brewing process. There are also a few wines and ciders available. Open from 11 am to 11 pm every day of the week with extended hours till 1 am on Friday and Saturday, Crooked Can Brewing Company is a great place to enjoy fine food and drinks.

Crooked Can Brewing Company

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

Website: Crooked Can Brewing Company

10. Stroll in Magnolia Park

Posted by Carsten Basile on Friday, 9 June 2017

Magnolia Park is located in Apopka, twenty minutes away from Winter Garden. It’s a beautiful park with trails, lovely scenery, and a butterfly garden. It’s also the site of many local festivals and concerts, so be sure to check the schedule before you come into town! Annual events include a bluegrass and folk music festival, a pumpkin fest, a hayride, an afternoon with Santa, and a wildlife festival. The park also offers weekly programs such as guided walks on sundays, eco adventures, and a campfire chat.

If you’d like to explore the rustic side of Winter Garden, you may also consider tent or RV camping at Magnolia Park. Don’t be surprised if you see peacocks wandering the park grounds. They draw many visitors to the park to see their vibrant colors.

Magnolia Park

Address: 2929 S Binion RD, Apopka, FL 32703

Website: Magnolia Park

11. Browse around Plant Street Market

Posted by Plant St. Market on Monday, 11 May 2015

Open seven days a week, Plant Street Market is like a permanent farmer’s market, full of unique and artistic vendors. With locally roasted coffee, farm-to-table food, cold pressed juice, hand-crafted chocolates and pastries, handmade apparel, decor, and jewelry, handmade candles, antiques, essential oils, bath products, and an oxygen bar, Plant Street Market has a little bit of everything from food to shopping.

It’s a great place to spend the afternoon sampling different foods and drinks while shopping for unique products. The market also hosts events, including concerts and festivals.

Plant Street Market

Address: 426 W Plant St, Winter Garden, FL

Website: Plant Street Market

12. Have some fun at Escape Goat LLC

Posted by Escape Goat on Friday, 8 April 2016

Have you ever been locked in a room with your friends and family and had to puzzle your way out, using wit and creativity? Now you can simulate this experience with an escape room.

Escape Goat offers three different rooms suitable for 2 to 6 players, so bring a crowd! Each room mimics a different scenario, and you’ll be “locked in” until you can figure your way out by cracking codes, finding hidden keys, and moving objects in the room. Escape Goat offers a Sherlock Holmes-themed adventure, an “Area 51” room, and summer camp haunted by a camp legend.

Escape Goat LLC

Address: 1165 E. Plant St., Winter garden, FL 34787

Website: Escape Goat LLC

13. Take a walk on the West Orange Trail

Editor's Note: There's no photo available at the time of writing

Spanning 22 miles (35 km), this paved trail passes through downtown Winter Garden and is a great place to stroll or bike. Whether you choose to take a short walk or bike the whole way, it’s a lovely way to enjoy Winter Garden.

West Orange Trail

Website: West Orange Trail

14. Learn about rail history at Central Florida Railroad Museum

Editor's Note: Photo taken from the establishment's official social account

The former freight room of the Tavares and Gulf Railroad now houses railroading artifacts from around Central Florida and the country!

Posted by Central Florida Railroad Museum on Friday, February 14, 2020

Located in a historic train depot in Winter Garden, this museum has dining car china, historic railroad cars, and other items of note. There are even climb-on cabooses and an interactive wooden train set.

Central Florida Railroad Museum

Address: 101 S Boyd St., Winter Garden, FL

Website: Central Florida Railroad Museum

15. Spend the day on the water at Lake Apopka

100's of wading birds gathered in a couple areas on the Lake Apopka Wildlife Drive 5/27/17. The Interceptor Road pond had mostly Great Egrets and Wood Storks.

Posted by Friends of Lake Apopka on Friday, 9 June 2017

The third largest lake in Florida, Lake Apopka is a great place to swim, boat, fish, canoe, or kayak. It’s a popular place to grab a vacation rental such as a cabin on the water. Be sure to stop by while you’re in Winter Garden!

Lake Apopka

Website: Lake Apopka

Winter Garden is full of summer activites

WOTwb WG arch
Source: Photo by user [Unknown] used under PUBLIC DOMAIN

With balmy temperatures all year long, outdoor activities like hiking at the nature preserve and enjoying the farmer’s market are always crowd pleasers. If you need to beat the heat, try cooling down with a beer or partaking in indoor activities like an escape room during your visit to Winter Garden!

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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A storyteller first and foremost, Hannah has a bachelor's degree in English Creative Writing and a fascination with the written word. Over the past several years, she's gained experience as a...Read more

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