23 Best & Fun Things to Do in Winter Garden (FL)

Winter Garden is a city located fourteen miles west of Orlando, which is about a twenty-minute drive from western Orlando.

This city was incorporated in 1908 and currently has a population of forty-four thousand, eight hundred and eighty-eight.

Winter Garden is a city rich in culture and history, offering numerous opportunities for adventure seekers to go out and have fun.

Some popular places in the city include Hagan O’Reilly’s Irish Pub, Tibet-Butler Nature Preserve, Winter Garden Village, Crooked Can Brewing Company, Bosphorous Turkish Cuisine, the Withers-Maguire House, Winter Garden Farmers Market, and more.

Are you planning an exploration of Winter Garden? Here are the top things to do in Winter Garden, FL.

Things to Do in Winter Garden, FL

1. Downtown Winter Garden

Downtown Winter Garden
Credits: Richard Elzey / Flickr
Downtown Winter Garden

A place where it all happens in Winter Garden is Downtown Winter Garden. Take a stroll through its streets and get a feel of the hustling and bustling in the city.

Downtown Winter Garden has something for everyone and offers a unique experience as you meet and interact with locals.

There are several unique stores that offer an array of dining options, shopping centers, and an amazing entertainment experience.

Downtown Winter Garden is a place that enormously promotes and showcases the city’s creativity, arts, and cultures.

There are also numerous stores in the area that offer different ranges of items such as fresh flowers, baked goods, artisan creations, specialty foods, locally sourced farm produce, and more.

You will find stores like the Home Goods & Gift Boutiques, Divine Wellness, The Boutique On Plant, Heirloom Amish Furniture, Garden Music School, Plantation Jewelers, Ruby & Rust Boutique, And More.

2. Garden Theatre

Garden Theatre
Credits: (Ebyabe) [CC BY-SA 2.5], Wikimedia Commons
Garden Theatre
At the top of your list of fun things to do in Winter Garden, FL should be a visit to Garden Theatre with your family and friends.

Garden Theatre was built in the 1930s as a non-profit center that offers patrons a wonderful experience through series of exciting events and more.

This theater is a venue for more than two hundred events such as films, musicals, theater, dance, and many more.

Garden Theatre was refurbished by Herbert J. Krapp with a seating capacity of more than one thousand, six hundred persons.

The theater is available for rentals for different occasions like meetings, screenings, weddings, and more.

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

3. Driftwood Market

Driftwood Market is a family-owned and operated business in Winter Garden that takes pride in the kinds of items offered.

This is a small store located in the downtown district of Winter Garden, offering wonderful customer service and the best products.

Driftwood Market holds honesty in great belief and gives customers opportunities to choose from various items with excellent quality and value.

From the moment you walk into the store, you will find numerous hand-curated collections, and the super friendly staff instantly make you feel like family, not as a stranger.

Driftwood Market is open on Monday & Tuesday from 11am-5pm, Wednesday & Thursday from 11am-6pm, Friday from 11am-7pm, Saturday from 10am-7pm, and Sunday from 12pm-4pm.

Address: 46 W Plant St, Winter Garden, FL 34787, United States

4. SOBO Art Gallery – Winter Garden Art Association

SOBO Art Gallery - Winter Garden Art Association
Credits: Syda Productions / Shutterstock

Are you an art fanatic? Add a visit to SOBO Art Gallery to your list of top things to do in Winter Garden, FL; it is worth the stop.

SOBO Art Gallery is one of the most popular art galleries in the state, and it is managed by Winter Garden Art Association.

Winter Garden Art Association is a non-profit organization dedicated to promoting community interests in education and cultural art.

The association plays an important role in the community’s cultural and educational sector by motivating every individual’s creativity.

SOBO Art Gallery showcases numerous art exhibitions of more than sixty pieces of artwork. The gallery holds lots of art workshops, art events, and art exhibits every month.

This art gallery provides a welcoming and friendly space for the public to come and explore, get enlightened, and have an amazing experience.

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

5. Winter Garden Village

Winter Garden Village
Credits: michaeljung / Shutterstock

For a stress-free and exciting buying experience, Winter Garden Village is the perfect destination for you in Winter Garden.

Winter Garden Village is an open-air retail location with more than one hundred retailers offering different kinds of merchandise and services.

Here, you will find everything you need without having to go to different locations, including dining and entertainment.

Winter Garden Village features stores like Barnes and Noble, JoAnn Fabrics, Men’s Warehouse, and many others.

There are several dessert stores, cafes, and sit-down restaurants offering a variety of dining options within the center.

You’ll also find fantastic retail stores like Target, Old Navy, HomeGoods, Cost Plus, UlTA, Lowes, World Market, Craft stores, etc.

Address: 3251 Daniels Rd, Orlando, FL 34787 United States

6. Winter Garden Heritage Museum

Winter Garden Heritage Museum
Credits: SPUI / Wiki (Public Domain)
Winter Garden Heritage Museum

For history enthusiasts, add a visit to Winter Garden Heritage Museum to your list of things to do in Winter Garden, FL.

Winter Garden Heritage Museum was established in 1983 to help preserve the city’s rich history.

This museum is located in the center of Winter Garden, featuring several historical artifacts relating to the development process starting from the early era to the current state.

Winter Garden Heritage Museum showcases historical items such as tools, ceramics, beads for trade, arrowhead points, and clay pipe fragments that promote the way of life of the Native Americans.

The Museum also features a 1950s fire engine, citrus sector equipment, a 1943 Cheshire caboose, and vintage agricultural tractors.

You will also learn more about medical history through the displayed Dr. Albert Gleason’s antique anesthetic equipment, his backpack, pharmaceutical bottles, and more from the 1940s.

Winter Garden Heritage Museum showcases ancient typewriters, barber equipment, telegraph machines, Doc Reeves, and more.

Address: 21 E Plant St, Winter Garden, FL 34787, United States

7. Our Nation’s Creations

Our Nation's Creations
Credits: G-Stock Studio / Shutterstock

Do you plan on going shopping? Add a visit to Our Nation’s Creations to your list of fun places to visit in Winter Garden, FL for a fantastic shopping time.

Our Nation’s Creations is a spot that features only products produced in the United States to support local businesses and passionate artisans.

Every item showcased at Our Nation’s Creations comes in high quality and long lasting durability for affordable prices.

Our Nation’s Creations offers a large selection of toys, T-shirts, jewelry, decor, unique gift items, and other items made in the United States.

The items displayed come in different kinds, colors, designs, and authenticity. Our Nation’s Creations staff is nice and helpful when attending to guests offering suggestions whenever confusion arises.

Address: OFFICE ONLY, 446 W Plant St, Winter Garden, FL 34787, United States

8. Tibet-Butler Nature Preserve

Tibet-Butler Nature Preserve
Credits: Timothy Holle / Shutterstock
Tibet-Butler Nature Preserve

Are you a nature-lover? Add a visit to Tibet-Butler Nature Preserve to your list of top things to do in Winter Garden, FL.

Tibet-Butler Nature Preserve is a place that every nature lover will appreciate, offering opportunities for people to come outside and have fun.

This Nature preserve features many trails going through wetlands and pine forests ideal for hiking and a way to enjoy the beautiful natural scenery and wildlife.

Tibet-Butler Nature Preserve trails are covered by several oak trees and pine trees and are ideal for both beginner and expert hikers.

This preserve features a lovely butterfly garden with an assortment of several butterfly species and offers essential information about wildlife and vegetation.

Tibet-Butler Nature Preserve is a beautiful place for intimate picnics, bird-watching, sightseeing, biking, and nature exploration.

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

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9. Central Florida Railroad Museum

Central Florida Railroad Museum
Credits: Ebyabe [CC BY-SA 2.5], Wikimedia Commons
Central Florida Railroad Museum
Central Florida Railroad Museum is an incredible museum in Winter Garden located in a historic train depot with many features.

This museum consists of several historic railroad cars and dining car china, including an innovative wooden train set and climb-on cabooses.

Central Florida Railroad Museum is open all days of the week from 1pm-5pm for everyone to explore and learn new facts.

The Museum also features original accounts, equipment, photographs, and many artifacts relating to unforgettable history of the advancement and railroads of the city.

Touring Central Florida Railroad Museum might take longer time than excepted, do well to visit the on-site gift shop and purchase unique treasures before leaving.

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

10. Winter Garden Farmers Market

Winter Garden Farmers Market
Credits: Brent Hofacker / Shutterstock

If you genuinely want to get a feel of the authentic Winter Garden’s local vibes, add shopping at Winter Garden Farmer’s Market to your bucket list of places to visit in Winter Garden, FL.

Winter Garden Farmer’s Market offers a wide range of fresh fruits, vegetables, handmade items, and more for affordable prices.

There are high-quality jewelry, herbs, baked foods, handmade soaps, meat, antiques, and other seasonal produce.

Winter Garden Farmer’s Market features numerous fun activities for families to participate in, including live music concerts, automobile exhibitions, and other events.

This market doesn’t just offer you opportunities to buy quality items but also allows you to meet and interact with locals to learn more about the community.

Address: Downtown Winter Garden, FL United States

11. Tucker Ranch

Tucker Ranch
Credits: FOTO Eak / Shutterstock

For a wonderful day out with your dear ones, add a day at Tucker Ranch to your list of things to do in Winter Garden, FL.

Tucker Ranch occupies a land space of two hundred and nine acres and a special evidence of how amazing nature is.

This nature center features a well-equipped playground with play equipment that keeps children excited.

Tucker Ranch consists of a nature trail ideal for hiking and walking, which are perfect ways to enjoy the beautiful scenery.

There are several reserved picnic areas excellent for an intimate moment with your family and friends; make sure you bring enough snacks and water.

Tucker Ranch also features a twelve-acre space called Tucker Ranch farm, which also serves as a teaching farm.

Address: 70 Tucker Rd, Winter Garden, FL 34787, United States

12. Plant Street Market

Plant Street Market
Credits: Chubykin Arkady / Shutterstock

One fun thing to do in Winter Garden is visiting Plant Street Market, a one-of-a-kind farmer’s market open seven days a week.

Plant Street Market features several vendors who are down to earth and offers nothing but the best products you can’t get elsewhere.

This market also offers a wide variety of hand-crafted chocolates, handmade apparel, bath products, pastries, jewelry, and decor.

You will also find top-quality oxygen bars, essential oils, handmade candles, antiques, and more. Plant Street Market features a good number of merchants that offer well-brewed juices and farm-to-table foods.

Plant Street Market hosts several kinds of events, festivals, and concerts you wouldn’t want to miss. Shopping at this market is also a great way to support local farmers and hard working businessmen and women in the community.

Address: 426 W Plant St, Winter Garden, FL United States

13. The French Café

The French Café
Credits: Brent Hofacker / Shutterstock
Italian sandwiche

Are you searching for a lovely restaurant to eat at? Add dining at the French Café to your list of places to visit in Winter Garden, FL.

The French Café is a highly recommended location that offers delicious breakfast meals prepared by professional chefs.

The meals served are made from scratch daily using high-quality locally sourced ingredients, which are the reason for their unique tastes and freshness.

The French Café offers a large food menu, including onion soup, chicken salad, Italian sandwiches, veggie crepe, croque madame, Breakfast Croissant with Swiss Cheese, Croissant Omelets Sandwiches, Strawberry and Cheese Danish, and more.

They also offer a wide variety of beverages, including coffee, teas, coke, and freshly pressed juices which come in different flavors according to your preferences.

Address: 16412 New Independence Pkwy #140, Winter Garden, FL 34787, United States

14. The West Orange Trail

West Orange Trail
Credits: SPUI / Wiki (Public Domain)
West Orange Trail

A perfect addition to your list of fun things to do in Winter Garden, FL is strolling down the West Orange Trail, a nice way to while time away.

The West Orange Trail is a well-paved trail that stretches to 35 km (22 miles), perfect for biking and walking, alone or with your pals.

This trail crosses the downtown district of Winter Garden and serves as a joint between suburban communities and the county’s urban.

The West Orange Trail starts at the Killarney Station trailhead to the downtown area and then Apopka, which ends at Welch Road.

15. Orange County National Golf Center and Lodge

Orange County National Golf Center and Lodge
Credits: pisitnamtasaeng / Shutterstock

Orange County National Golf Center and Lodge is one of Winter Garden’s best golf courses, attracting golf lovers from different parts of the country.

The golf course is fully equipped and adequately maintained, featuring two championship courses and a nine-hole short course.

Orange County National Golf Center and Lodge also feature one of the country’s biggest driving ranges and practice areas.

There is a grill spot that offers delectable meals prepared on-site and chilled drinks to boost your energy when you begin to feel drained.

Orange County National Golf Center and Lodge also feature a well-stocked gift shop with different golf equipment and apparel.

Address: 16301 Phil Ritson Way, Winter Garden, FL 34787, United States

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16. The Withers-Maguire House

Withers-Maguire House
Credits: Ebyabe [CC BY-SA 2.5], Wikimedia Commons
Withers-Maguire House
 The Withers-Maguire House in Winter Garden was built by David Maguire and General William T. Withers in 1888.

The House was later sold to the city and was listed on the National Register of Historic Buildings in 1987 due to its role in promoting the town’s history.

The Withers-Maguire House is beautifully decorated with several historic displays dating back to the 1800s.

This home gives visitors insight into the era when Winter Garden was underdeveloped and based entirely on agriculture.

The Withers-Maguire House consists of authentic and well-refurbished housewares, art, and furniture, making it a perfect venue for weddings and events.

This is an excellent place to while away time, and it is always open on Saturdays and Sundays from 2pm to 4pm for free.

Address: 16 East Oakland Avenue, Ocoee, FL 34761 United States

17. Cinépolis

Cinépolis
Credits: Dean Drobot / Shutterstock

Cinépolis is a movie theater in Winter Park and a popular destination for movie fans who want to have a great time while watching their favorite blockbuster movie.

This movie theater features a cutting-edge projection with a great sound system and fully-reclining leather seats for better comfortability.

Cinépolis is a beautifully decorated theater that offers a vibrant and energetic ambiance for the guests to feel free and have a good time.

There is a full bar in the area that offers a wide variety of beverages and a comprehensive gourmet menu that offers delectable meals and snacks.

Address: 14111 Shoreside Way, Winter Garden, FL 34787 United States

18. Crooked Can Brewing Company

Crooked Can Brewing Company
Credits: givaga / Shutterstock

Crooked Can Brewing Company is a wonderful family-friendly location making it a great place to spend time with your family and friends.

This brewery is a highly recommended destination that offers nothing short of delicious meals and unique drinks.

Crooked Can Brewing Company offers an impressive collection of beers with great quality and tastes, such as high stepper, Florida sunshine, cloud chaser, up yondea, domestic ales, citrus kicker, and more.

They offer a menu with nice meals to match the drinks served, including Poutine, Cheese Covered Potatoes with Bacon, Pork Fries, burgers, sushi, pizza, wings, and so on.

Crooked Can Brewing Company offers brewery tours which give guests a chance to try out new flavors and see how the drinks are processed.

The brewery is usually open all days of the week from 11am-11pm; make sure you stop by to enjoy a drink and delicious food.

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

19. The Attic Door

The Attic Door
Credits: gresei / Shutterstock

The Attic Door is a lovely live music venue in Winter Garden with a full-service wine bar that offers you a place to spend time with your loved ones.

This wine bar is known for keeping everything simple, and classic starting with the meals served to the drinks offered.

The Attic Door offers a comfortable environment with cozy furniture and well-designed decorations, attracting many visitors.

They offer a small food menu that features delicious meals such as Hot Spinach & Artichoke Dip, Egg Sausage Burrito with Queso, Nasi Goreng, Berry French Toast, Tuscan Bruschetta w Feta, Fruit and Cheese Plate, and more.

The Attic Door offers an extensive drink menu, including stone ruination double IPA, chimay blue trappist ale, magners pear cider, bourbon infused cherry, bud light, strawberry lime cider, chocolate raspberry wine, and lots more.

The Attic Door is open from Tuesday to Thursday from 4pm-10pm, Saturday from 11am-11pm, and Sunday from 11am-1:30pm. (Closed on Monday)

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

20. Escape Goat LLC

Escape Goat LLC
Credits: WillemijnB / Shutterstock

Escape Goat LLC is a place in Winter Garden that will let loose your creative spirit and challenge your logical and fast thinking skills.

This family-friendly center offers a whole new experience that will definitely be one of the major highlights you won’t forget easily.

Escape Goat LLC features three separate rooms perfect for as low as two to a maximum of six players, although each room has its uniqueness and challenges.

You and your team members will be locked in a room and go about searching for keys, finding clues, cracking codes, and more that will enable you to escape the room.

Escape Goat LLC features rooms with different concepts such as summer camp haunted by a camp legend, an “Area 51” room, and Sherlock Holmes-themed adventure.

You can also host your special events here, such as wedding parties, family get-togethers, and birthday parties in this attraction.

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

21. Hagan O’Reilly’s Irish Pub

Hagan O'Reilly's Irish Pub
Credits: Hagan O’Reilly’s / Facebook
Hagan O’Reilly’s Irish Pub

When you feel like hanging out with your friends, add a visit to Hagan O’Reilly’s Irish Pub to your list of fun things to do in Winter garden, FL.

Hagan O’Reilly’s Irish Pub is a stylish Irish pub that offers everything you need to have an incredible experience.

They serve delectable dishes, and tasty drinks in a casual setting coupled with a welcoming environment.

Hagan O’Reilly’s Irish Pub features a cozy patio, ping table, a fireplace, and TVs, making it a perfect place to play games, watch live matches, and have a great time.

The comprehensive food menu includes chicken tenders, shepherd pies, the Reuben, fish N chips, grilled cheeseburgers, bacon cheeseburger, corned beef & cabbage, nachos, meatloaf, mozzarella sticks, grilled chicken wrap, Irish house salad, and more.

Hagan O’Reilly’s Irish Pub offers a variety of beers on tap, including domestic and imported drinks such as Yuengling gold, sailfish, Heineken, colors light, Blue Moon, big storm, michelob ultra, iron city light, and others.

Address: 16112 Marsh Rd, Winter Garden, FL 34787 United States

22. Bosphorous Turkish Cuisine

Bosphorous Turkish Cuisine
Credits: Bosphorous Turkish Cuisine – Winter Garden / Facebook
Bosphorous Turkish Cuisine

An excellent addition to your list of things to do in Winter Garden, FL is visiting Bosphorous Turkish Cuisine with loved ones.

Bosphorous Turkish Cuisine is a unique restaurant that serves delicious Turkish foods hand crafted using special techniques by well-skilled and passionate chefs.

They ensure that all veggies and meats used in the preparation of the meals are fresh and of great quality; almost all the ingredients are sourced from Turkey.

Bosphorous Turkish Cuisine is well designed with beautiful paintings, antiques, silk carpets, Mediterranean pottery, and more.

They serve meals like white bean salad, red lentil soup, shrimp casserole, grilled sea bass, chicken adana kebap, stuffed cabbage, sautéed eggplant, grilled lamb adana kebap, and more.

Bosphorous Turkish Cuisine is open from Sunday to Thursday from 11am-10pm, and Friday & Saturday from 11am-11pm.

Address: 108 S Park Ave, Winter Park, FL 32789, United States

23. Kaebisch Chocolate

Kaebisch Chocolate
Credits: Dmitr1ch / Shutterstock

Are you ready for some mouthwatering treats? Add a visit to Kaebisch Chocolate to your list of things to do in Winter Park.

Kaebisch Chocolate is a lovely store that offers everything from handmade chocolates prepared using raw materials.

These chocolates come in different textures and flavors, respectively, with excellent quality and freshness. Kaebisch Chocolate is owned by Anna Kaebisch Burnett and her husband, who simply wanted to serve patrons fresh chocolate.

Kaebisch Chocolate offers a wide range of bonbons, truffles, cakes, fresh herbs, fresh citrus fruits, Caribbean espresso, and more.

They also offer items like orange peel dipped in chocolate, macarons, raspberry, Earl grey tea, and other delightful treats.

Kaebisch Chocolate staff is super friendly and nice, offering a welcoming atmosphere for customers to come and have a nice treat.

Address: 50 W Plant St #3140, Winter Garden, FL 34787, United States

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Plan a Trip to Winter Garden

Winter Garden is an incredibly beautiful city with several mind-blowing attractions and exciting activities to try out.

So you do not have to worry about fun things to do in Winter Garden, FL, as this list is here to guide you through and ensure you have a great time.

Winter Garden is a perfect vacation destination for families, friends, spouses, or even individuals. Start planning a trip to this city today!