15 Best Things to Do in Winter Garden

Located west of Orlando in Florida’s Orange County, Winter Garden is a key city in the Orlando, Kissimmee and Sanford metropolitan area and had a population of about 35,000 at the time of the last census.

Known for its proximity to many of the state’s most popular theme parks, for much of its existence, the area around Winter Garden was full of large citrus farms.

Scenic Lake Apopka nearby offers visitors a variety of recreation options; whether you’re into cultural, artistic or natural attractions, finding things to see and do won’t be a problem.

Below are 15 things to do in and around Winter Garden, Florida.

1. Winter Garden Farmer’s Market

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Source: Winter Garden Farmers Market / Facebook

Winter Garden Farmers Market

With abundant sunlight and rain and a growing season that lasts for much of the year, it’s no surprise that Winter Garden and Florida in general are some of the country’s most abundant fruit and vegetable producers. For those looking to have access to all those seasonal fruits and vegetables in one location, the Winter Garden Farmer’s Market would be a great place to check out.

In addition to its produce, the market offers live events, fairs, festivals, and lots of other family-friendly entertainment options.

Located in the downtown area, it’s open every Saturday from 9 AM until 2 PM.

2. Crooked Can Brewing Company

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Source: Crooked Can Brewing Company / Facebook

Crooked Can Brewing Company

Nothing tops off a long day on your feet in the sweltering Florida sun better than a cold brew, and when it’s brewed locally and with natural ingredients, so much the better.

Located on West Plant Street in Winter Garden, Crooked Can Brewing Company is known for its relaxed environment, helpful staff, and great food that includes burgers, sushi, wings, and even a few vegan options.

They offer a variety of beers that come in an array of flavor profiles, so try a sampler to see what you like before ordering a pint or two.

Consider a guided brewery tour to learn about the beer-making process.

3. Plant Street Market

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Source: Plant St. Market / Facebook

Plant Street Market

For those who’d rather not spend their hard-earned travel dollars at a national retail chain without much local character, a visit to the Plant Street Market would be the perfect antidote.

Open seven days a week, it is full of a variety of vendors selling artsy, chic, and bohemian items of nearly every description.

The market is also well-known for its homemade chocolates and pastries, coffee, baked goods, and locally made health and body products.

Not only is it a fun place to visit, but buying a thing or two will help local farmers, artists, and entrepreneurs, and most of the money will stay in the area.

4. Tibet-Butler Nature Preserve

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Source: Timothy Holle / shutterstock

Tibet-Butler Nature Preserve

Located just down the road in Orlando, Tibet-Butler Nature Preserve is the area’s premier destination for those who’d like to experience the unique Florida pine forests and swamplands that are not only beautiful, but home to a fantastic number of plant and animals species as well.

Featuring a variety of trails – the longest of which is nearly four miles – the park is a favorite of hikers and bikers, bird-watchers, picnickers, and all-around nature enthusiasts.

There’s a popular butterfly garden onsite too, which is a perennial favorite of families traveling with insect and animal-loving children.

Check the welcome center before heading out on your own.

5. Withers-Maguire House

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Withers-Maguire House

Located on East Oakland Avenue in nearby Ocoee, the Withers-Maguire House is just a few minutes from Winter Garden and was built more than 120 years ago.

The home and most of its furniture, art, and housewares are original or have been restored to near-perfect condition, giving visitors a unique historical insight into a time when the area around Winter Garden was largely agricultural and undeveloped.

The home is open on Saturday and Sunday afternoons and is free to visit, making it both convenient, educational, and easy on the wallet.

Most guests end up spending about an hour to see everything.

6. Escape Goat

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Source: Escape Goat / Facebook

Escape Goat

Escape rooms have burst onto the recreation scene in recent years. For those who’ve never experienced the thrill and suspense, Escape Goat on East Plant Street in Winter Garden would be a great place to have your first experience of this exciting new form of entertainment.

Featuring a variety of distinctly themed rooms, Escape Goat strives to simulate real-world emotions, and most guests are surprised at just how heart-pounding the whole production is.

Escape rooms are great double-date ideas and are good for birthday parties, family reunions, and wedding parties.

Reserve your spots in advance if possible.

7. Central Florida Railroad Museum

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Source: Central Florida Railroad Museum / Facebook

Central Florida Railroad Museum

The Central Florida Railroad Museum in Winter Garden is housed in the historic depot of a now-defunct railway and is open every day except holidays from 1 until 5 PM.

The museum is located on South Boyd Street and is a particularly relevant destination for history, railroad, and transportation buffs. The items on display include equipment, photographs, first-hand accounts, and other unique bits of local history pertaining to the area’s development and railroads.

You probably won’t need to set aside more than an hour, and don’t forget to check out the museum’s gift shop for a unique keepsake or two before heading off to your next adventure.

8. The Wheel At ICON Park Orlando

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Source: Woody Woods / shutterstock

The Wheel At ICON Park Orlando

Those in the know claim that The Wheel At ICON Park Orlando wheel was constructed using techniques that give it one of the smoothest rides of any Ferris wheel you’ll find anywhere.

The Eye’s gondolas are stabilized, air-conditioned, and offer amazing vistas of the surrounding areas that those stuck on the ground can only dream of.

When the weather cooperates, it’s possible to see as far as Cape Canaveral, which is known for its NASA space launch facility.

The area around the Eye hosts a variety of live entertainment, fairs, and festivals too, making it the kind of place many travelers choose to spend significant amounts of their vacation time.

9. House of Blues Orlando

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Source: J.A. Dunbar / shutterstock

House Of Blues Orlando

House of Blues Orlando can really draw the crowds, and in addition to its live music, it’s also well-known for its relaxed setting, tasty drinks, and yummy fare, including traditional favorites like burgers and wings as well as seafood, soups, and salads.

House of Blues features a variety of local, regional, and nationally known artists, so the best way to keep up to date is to check the calendar of events on their website periodically.

Daily happy hour drink and food specials make it a popular destination both during the week and on the weekends, so stop by and enjoy some great music and rub elbows with some locals.

10. Merritt Island National Wildlife Refuge

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Source: Dimitris Timpilis / shutterstock

Merritt Island National Wildlife Refuge

At nearly 150,000 acres, the Merritt Island National Wildlife Refuge is big by any standards. It’s home to thousands of species of plants and animals, many of which are unique to the area.

One of the refuge’s most popular attractions is the Manatee Observation Platform, from which it’s often possible to view the large marine mammals that dine on aquatic vegetation and are typically referred to as sea cows.

A number of admission options are available, including single day, seasonal, and multiple location options, so check their website carefully to see what makes the most sense for you before making a special trip.

11. World’s largest McDonald’s

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Source: Nixx Photography / shutterstock

World’s Largest McDonald’s

Though it may not be a popular vacation destination for those counting their calories or trying to reduce their cholesterol, a visit to the world’s largest McDonald’s is still one of those unique bits of local Americana that many travelers think is worth checking out, even if only for a quick bite before charging off to a new adventure.

In addition to being the largest McDonald’s restaurant, it’s shaped like a box of French fries and is a favorite photo-op for lovers of the famous fast food brand.

The restaurant can draw the crowds, so don’t expect to have the place to yourself. If you’re all burgered out, they sell non-traditional food items like pizza and pasta too.


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Source: Icebar Orlando / Facebook


Though it’s more reminiscent of what you might expect to find in a Scandinavian country in winter, Orlando’s ICEBAR is a refreshingly unique and chilly place that’s a real standout with many visitors.

Since most Sunshine State visitors don’t bring coats and gloves, guests will be provided with them upon entering. When the cold drinks and even colder air get to be too much, most guests slip next door to the Fire Lounge, that’s known for its trendy music, fashionable clientele, and hot dance floor.

There’s no cover charge to visit either ICEBAR or Fire Lounge. Daily drink specials are offered, and there’s usually a live DJ too.

13. The Museum of Military History

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Source: Museum of Military History / Facebook

Museum Of Military History

Located in nearby Kissimmee an easy drive from the Winter Garden area, the Museum of Military History is dedicated to honoring the sacrifices made by the men and women of the armed forces.

The museum’s exhibits cover the period from the Revolutionary and Civil Wars through Vietnam, Korea, and the Gulf and Afghanistan conflicts.

The items on display include uniforms, weapons, photographs, and poignant first-hand accounts of those who served in a variety of roles.

New artifacts and memorabilia are constantly being added by acquisition and donation, so consider making a small monetary contribution to help them in this effort.

14. Fish Orlando Trophy Bass Guide Service

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Source: M Huston / shutterstock

Fish Orlando Trophy Bass Guide Service

Florida has always been a fishermen’s paradise, and it’s especially so for those freshwater anglers who come from all over the country to try their hand at landing massive Florida-strain largemouth bass.

The bass in Lakes Toho and Harris and the St. Johns River grow to epic proportions, and the area hosts a variety of amateur and professional fishing tournaments throughout the year.

Fish Orlando Trophy Bass Guide Service offers guests a number of package options, including live bait and artificial lure fishing in full and half-day outings available in the morning, afternoon and evening.

You’ll need a valid Florida fishing license whether you’re an in-state resident or visitor.

15. Gatorland

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Source: James Kirkikis / shutterstock


Located on South Orange Blossom Trail in Orlando, Gatorland is one of the state’s most well-known and often-visited destinations. It’s perfect for those who’ve got the guts to get up close and personal to some rather large and toothy predators that are known for their ornery dispositions.

Gatorland offers a variety of educational programs and regularly scheduled feeding shows, and there’s an onsite aviary and petting zoo as well.

Due to its popularity, Gatorland can get pretty crowded during peak times, so if you’d like to avoid the hordes, consider visiting during the week or in the off-season.

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