Blake Walsh

15 Best Things to Do in Winter Garden, FL

  • Published 2021/12/08

Winter Garden is an idyllic lakeside community, a 20-minute drive west of Orlando.

The town, established in 1908, has more than 40,000 citizens today.

Winter Garden is well-known for its wide range of recreational opportunities, cultural events, and historical landmarks, all of which contribute to the city’s allure as a destination for residents and tourists.

Its historic downtown is on the National Register of Historic Places.

What’s the story behind the town’s moniker?

When the three Seminole Wars ended in the mid-1800s, many farmers from the Deep South moved to the area.

Winter Garden’s downtown did not come to life until its founders established two railroads along Plant Street in 1899.

According to folklore, railroad employees have spat tomato seeds into the ground.

Sometime later, they discovered tomato plants.

In the winter, they would write home to tell their loved ones how lovely it was and how it wasn’t cold.

They said, “You can even have a garden throughout the winter!”

There are many reasons why Winter Garden is a great place to live, work, and visit.

Small shops, historic downtown, and the Winter Garden Village at Fowlers Grove, a leading retail center with over one million square feet, all contribute to a vibrant business community in Winter Garden.

Winter Garden is home to more than 2,000 enterprises.

The city is bustling with small enterprises and entrepreneurs.

There is a wide range of recreational activities to choose from in Winter Garden, whether you’re interested in cultural, artistic, or natural attractions.

Read on to discover what this place has to offer.

Explore the City’s History at Winter Garden Heritage Museum

View of Winter Garden Heritage Museum

SR Productions /

The Winter Garden Heritage Museum, completed in 1983, is a 501(c)(3) organization.

The museum lies in the Atlantic Coast Line terminal, erected in 1918.

To preserve the town’s rich history, the Heritage Museum stands in the heart of Winter Garden.

View of Winter Garden Heritage Museum

Ebyabe, CC BY-SA 3.0, via Wikimedia Commons

Local fruit labels, a model citrus packing house, and an audio kiosk are all part of their diversified collection of artifacts and activities on architectural preservation.

It also displays Lake Apopka’s history and current restoration as “the large-mouth bass capital.”

War posters accompany images from the past depicting combat heroes.

View of Winter Garden Heritage Museum

Ebyabe, CC BY-SA 3.0, via Wikimedia Commons

The museum also has an abundant collection of antiques from its early days and its successful development throughout the pioneer settlement years.

There will be a display of artifacts from the Native American way of life, including ceramics, beads for trade, tools, clay pipe fragments, and arrowhead points.

View of Winter Garden Heritage Museum

SR Productions /

The museum is a 1943 Cheshire caboose, a 1950s fire engine, and vintage agricultural tractors and citrus sector equipment.

You will also find old telegraph machines, typewriters, adding devices, and Doc Reeves’ barber equipment here.

It also features a section about medical history featuring the 1940s Dr. Albert Gleason’s pharmaceutical bottles, antique anesthetic equipment, and his black bag.

View of Winter Garden Heritage Museum

Ebyabe, CC BY-SA 3.0, via Wikimedia Commons

Browse Different Shops at Winter Garden Farmers Market

Because of the year-round abundance of sunshine and rain in Downtown Winter Garden, there is such an ample supply of fresh fruits and vegetables.

From 9 a.m. to 2 p.m. every Saturday in Downtown Winter Garden, there is a Farmer’s Market where you can get your hands on some of the most distinctive seasonal fruits and veggies available.

In addition to fresh fruits and vegetables, meats, handcrafted soaps, herbal tea, street cuisine, jewelry, handicrafts, and antiques, the market holds several family-friendly fairs, festivals, and other events throughout the year.

There are a variety of activities to choose from, including live music performances, automobile exhibitions, and more.

Farmer’s market visitors and locals alike spend their time at the market.

Tour the Central Florida Railroad Museum

This Railroad Museum stands at the former depot of the now-defunct rails.

Every day except holidays, the Central Florida Railroad Museum is open from 1 p.m. to 5 p.m.

People visit the museum on South Boyd Street because it is a popular destination for history buffs, train lovers, and anyone interested in transportation.

To learn more about the area’s rich railroad history as well as Winter Garden’s place in it, visitors may peruse the museum’s extensive collection of pictures, artifacts, and other memorabilia.

The museum also features an interactive wooden train set and climb-on cabooses.

Gaze at Local Masterpieces at SOBO Art Gallery

A historic building in Winter Garden, the Old Fire Station formerly housed the city’s recreation department before serving as various businesses.

It serves as the new SOBO Art Gallery, home to the Winter Garden Art Association.

Its objective is to foster individual creativity and creative expression, community engagement and collaboration, and the visual and cultural arts’ awareness, education, and accessibility via its programs.

SOBO Art Gallery is the most well-known gallery in Central Florida.

Since its inception, the gallery has hosted several shows in which it has received more than 200 entries, displaying 50 to 60 works of artwork.

Buy Organic Products From Plant Street Market

View of Plant Street Market

SR Productions /

You may have a good time for nothing at the Plant Street Market in Winter Garden.

Plant Street Market is an excellent spot to spend a day sampling a variety of snacks and beverages, seeing unusual artworks and handiwork, as well as making a few purchases if you’d like.

View of Plant Street Market

SR Productions /

Throughout the week, the Plant Street Market offers a wide variety of handmade goods from various artists and craftspeople, including locally roasted coffee, fresh produce, a variety of juices and smoothies, handcrafted chocolates, and pastries, candles, and personal care products.

This market also hosts music and cultural shows, exhibits, and festivals.

To support local farmers and artisans put on the Plant Street Market, we recommend that you purchase something from their wares.

View of Plant Street Market

SR Productions /

Enjoy an Afternoon at Crooked Can Brewing Company

Even better than an ice-cold brew in the blazing Florida heat is one made using locally sourced and organic ingredients.

Crooked Can Brewing Company in West Plant Street is well-known for its laid-back atmosphere, friendly employees, and delicious cuisine, including sushi, wings, burgers, and vegan choices.

Try a sampling to discover something you like before purchasing a whole pint or two since they have a wide selection of beers with different flavors and aromas.

A brewery tour is a great way to learn more about the process of creating beer.

Solve Mysteries at Escape Goat

Have you ever been trapped in a room and relied on wit and ingenuity to escape?

The advent of the escape room allows you to re-create this experience in your own home or office.

Bring a large group to Escape Goat, as three different rooms can accommodate anything from two to six people.

You’ll be “locked-in” until you break the codes, uncover the hidden keys, and move the items in the room to find a way out.

In addition to the “Area 51” level, Escape Goat has a spooky summer camp and a Sherlock Holmes-themed adventure.

Hike Along the West Orange Trail

Orange County’s West Orange Route is a premier rail trail that connects the county’s urban and suburban communities.

Outposts and Stations, located along the path, provide parking and restrooms, with the Stations having a more fantastic range of amenities.

The route begins at the Killarney Station trailhead and travels through Winter Garden and Apopka before terminating at Welch Road in Apopka.

Walking or bicycling the whole 22-mile length of this paved route, which runs through the heart of Winter Garden, is a breeze.

It’s a great way to see Winter Garden, whether you stroll or ride your bike the whole way.

Other Things to Do Nearby

Explore the Tibet-Butler Nature Preserve

View of Tibet-Butler Nature Preserve

Timothy Holle /

The paths of the Tibet-Butler Preserve go through pine trees and swamps that are distinctive to the state of Florida.

The Tibet-Butler Preserve is first on our list of places to see around Winter Garden and Orlando that are rich in wildlife and flora.

As a result of its abundance of rare and unusual plants and animals, it is a popular vacation spot for ecotourists and other outdoor enthusiasts.

View of Tibet-Butler Nature Preserve

Katie Sanchez /

This wildlife refuge in Orlando is available to the public and is a favorite destination for visitors and locals alike.

It has a number of paths, including one about four miles long.

It is a popular destination for hikers, cyclists, birdwatchers, and nature enthusiasts.

Families with children interested in insects and nature can have a pleasant lunch here.

View of Tibet-Butler Nature Preserve

Timothy Holle /

A butterfly garden that caters to youngsters and adults alike should not be overlooked.

In addition, there is a nature preserve where visitors may learn more about the local flora and fauna.

Winter Garden’s Tibet-Butler Nature Preserve is a great spot to go back to nature and should be on your itinerary if you’re in the area.

Visit the Withers-Maguire House

View of Withers-Maguire House

(Ebyabe), CC BY-SA 3.0, via Wikimedia Commons

Withers-Maguire House lies 12 minutes from Winter Garden.

This house, completed more than a century ago, is one of Ocoee’s most historic properties.

The house, along with its furnishings, art, and kitchenware, has been meticulously restored to its original state.

View of Withers-Maguire House

Ebyabe, CC BY-SA 3.0, via Wikimedia Commons

Aside from being handy and instructive, you may also save money by visiting on Saturday and Sunday afternoons.

Most visitors spend about an hour and a half touring this house on average.

Relax in Magnolia Park

View of Magnolia Park

Jeff Holcombe /

When it comes to Winter Garden’s natural wonders, Apopka’s Magnolia Park stands out.

The park is just a twenty-minute drive from Winter Garden and has stunning trails, landscapes, and a lovely butterfly garden.

On the weekends, the park offers eco-adventures, guided tours, and campfire talks as part of its weekly programming.

View of a Bird in Magnolia Park

Jeff Holcombe /

You could get fortunate enough to observe them walking through your campground.

End your hunt for a nature-filled adventure here at Magnolia Park.

Before making travel arrangements, you may take note of all of their upcoming festivals and events on their website.

View of Magnolia Park

Jeff Holcombe /

Many visitors drive from as far away as Orlando to spend the night, snap photos, and spread the word about the beauty of Winter Garden’s Apopka Lakes Park.

We assure you that a visit to this park will be one of your most memorable experiences.

View of a Bird in Magnolia Park

Jeff Holcombe /

Check Out the World’s Largest McDonald’s

Even for those who don’t care about their health, the world’s largest McDonald’s, is still a must-see for those who want to see a slice or two of Americana before embarking on a new journey.

This store stands along 7344 W Sand Lake Rd., Orlando, just 23 minutes away from Winter Garden.

On top of that, it has become a famous picture op among McDonald’s lovers because of its unique design: it looks like an enormous package of fries.

Do not expect to have the restaurant to yourself, since it might attract few visitors.

Pizza and spaghetti are also available if you’ve had enough burgers.

Admire the View of the Region on the Wheel at ICON Park Orlando

View of  ICON Park Orlando

LnP images /

The Wheel is about a 25-minute drive from Winter Gardens.

With its smooth ride, the ICON Park Orlando Ferris wheel is one of the best you’ll ever experience.

Air-conditioned gondolas on the Eye provide passengers with views of the surrounding region that those stranded can only imagine at ground level.

View of  ICON Park Orlando


If the weather is clear enough, you can see Cape Canaveral, famous for its NASA space launch site.

The Eye’s area features a wide range of musical performances, fairs, and festivals, making it a popular destination for tourists.

Pay Tribute to Heroism at the Museum of Military History

Winter Garden residents may easily travel to Kissimmee to visit the Museum of Military History, 38 minutes away from the city, in commemoration of the men and women who have given their lives for their country.

In addition to the Revolutionary and Civil War eras, the museum’s displays include the Korean War, Vietnam War, Gulf War, and Afghanistan battles.

You may see old uniforms, weaponry, and tragic first-hand testimonies of soldiers at the museum.

Consider making a modest donation to assist the museum in acquiring and preserving new items and memorabilia.

Watch Impressive Performances at House of Blues Orlando

View of House of Blues Orlando

Jose Garcia, CC BY-SA 2.0, via Wikimedia Commons

Visitors to House of Blues Orlando come for more than just the live music; the venue is well-loved for its laid-back atmosphere, delectable cocktails, and mouthwatering meal, including conventional pub fare and more creative dishes like seafood and salads.

House of Blues, located 33 minutes away from Winter Garden, hosts a wide range of local, regional, and national musicians, so the best way to stay up to date is to visit their website often.

Drop by for some fantastic music and a chance to meet some locals during happy hour on weekdays and weekends alike.

Final Thoughts

It’s easy to see why so many people return to Winter Garden year after year.

There is no shortage of things to do in this fascinating metropolis and its surrounding areas.

You’ll find something you like in this city, no matter what your interests are.

Plan your trip to Winter Garden using our list of best things to do in this city.

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