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Best Things to Do in Winter Garden

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The best part about Orlando is knowing that there are so many neighborhoods and communities full of cool, unique treasures. Winter Garden is one of those places.

Just 30 minutes West of Downtown Orlando, Winter Garden is full of food, art, and events that locals and visitors can enjoy.

Farmers markets, art exhibits, coffee, Lake Apopka, and the bustling energy on a Saturday in Historic Downtown Winter Garden is a fun-filled experience you won’t want to miss!

Keep reading to find all the best places along Plant Street. 

Grab A Bite


📷 Katie Schwartz

129 W Plant St, Winter Garden, FL 34787

It’s nearly impossible to pass up Mexican food when you come across it. Lucky for you, you can stop by The Whole Enchilada while you explore Winter Garden. It’s classic Mexican cuisine with a trendy twist.  

You can go classic with their tacos and burritos or change it up by ditching the tortilla and swapping meat for tofu. All to say, if you prefer classic Mexican food or if you have allergies or picky eaters in the family, everyone will be able to find something tasty here!

Don’t forget to finish off your meal with Sopapillas, fried flour tortillas topped with cinnamon and sugar then drizzled with honey. And snap a pic for your foodie Instagram!

426 W Plant St, Winter Garden, FL 34787

Who doesn’t love cheese-covered pasta? Mac’d Out is a specialty mac and cheese stand located at the Plant Street Market. They provide the freshest pasta and made-to-order mac and cheese dishes.

You’ll fall in love with the comfort of typical mac and cheese while also appreciating the artisan twist. You can create your own dish with proteins and “fun stuff” (veggies) or choose one of their unique creations like Southwest or Mac’d Philly!

Roper Garden Building, 146 Plant St, Winter Garden, FL 34787

If you’re looking for delicious American cuisine that uses the seasons as an influence, then you will love Market To Table. It’s a casual, yet upscale restaurant right in the heart of Historic Downtown Winter Garden, behind the Garden Theatre.

It’s a unique place with wonderful service. It has a very relaxed energy and you’ll have nice, unwinding experience. You’ll enjoy grabbing a bite here with the family!

99 W Plant St, Winter Garden, FL 34787

Located in the historic Edgewater Hotel, Chef’s Table is the place for you if you’re looking for a more fine dining experience. It’s intimate, quaint, and known for its gourmet dining experience. It’s a wonderful place for date night and will expose you to the freshest seasonal ingredients and the true passion of their chef.

They offer a three-course dinner with a fixed price and an impeccable wine list. Essentially, you just get to sit back and relax while your new favorite dishes are prepared for you!

Drinks & Happy Hour

📷 Crooked Can

426 W Plant St, Winter Garden, FL 34787

Also located inside Plant Street Market, Crooked Can Brewing Company is one of Orlando’s local breweries where people come to experience the blend of classic techniques and unconventional practices that create their perfect, full-bodied beers. It’s a fun, cheery environment for a night out with friends or a relaxed Saturday afternoon with the family.

Their unique craft beer is absolutely delicious and consistent in quality. You can tell the brewmasters are passionate about bringing customers local Florida brews!

146 W Plant St #120, Winter Garden, FL 34787

Right next to the Garden Theatre, Pilars Martini asks you to enjoy an evening of “martinis, mixology, music, and more.”

The drinks are creative, with a fun twist on an extensive menu. They often have live music and also have a phenomenal appetizer menu, so it’s the perfect spot for drinks and a bite to eat before or after a show at the theatre. You’ll absolutely love the atmosphere as you enjoy what are arguably the best drinks in Downtown Winter Garden.

The Sunday JazzJam is an evening you’ll want to experience for yourself. They’re family-friendly on the weekends and have nice outdoor seating that’ll make you want to stay forever!

28 W Plant St, Winter Garden, FL 34787

If you’re wandering Winter Garden and find that it’s time to wine down, The Attic Door has you covered. This eclectic and cozy wine bar provides the best live music, wine, and menu offerings for your evenings.

What’s even cooler about this spot is that it doubles as a tea room on the weekends. Afternoon tea is by reservation only and they offer scones with house clotted cream, finger sandwiches, savories, and desserts.

It’s an enchanting experience that will make the quaint and charming environment of Historic Winter Garden even more inviting.

Coffee, Art, & Culture


📷 Winter Garden Farmers Market

104 S Lakeview Ave, Winter Garden, FL 34787

If you’re looking for an endearing way to spend your Saturdays with the family, the Winter Garden Farmers Market is your answer. It takes place right in the Historic District of Winter Garden and has grown to a community staple and offers a massive selection of vendors including baked goods, locally grown produce, fresh flowers, homemade soaps, artisan crafts, and more!

Families (including the members with four legs) are welcome to wander and enjoy the live music and tasty treats in this homey and whimsical setting.

146 W Plant St #110, Winter Garden, FL 34787

If you know about Orlando’s coffee scene, then you’ve probably heard someone mention Axum Coffee. It’s a colorful cozy spot to grab a hot or iced beverage. Going to Axum is even more enjoyable because all of their profits go to towards charitable causes.

It’s a great place to study, hang out with friends, or just to pick up an iced latte before exploring the streets of Winter Garden. You’ll always have impeccable service and experience a sense of home at this feel-good coffee cafe!

127 S Boyd St, Winter Garden, FL 34787

The Winter Garden Art Association has a goal to be a part of the cultural and educational practices in the community. They strive to be a positive impact on the City of Winter Garden. They achieve this through the SOBO Art gallery, also located in the historic part of town.

Here, you can experience a plethora of exhibits for free. They also offer kid and adult art programs, so everyone can have fun and be creative. They also host countless events throughout the year, so you can always find things to do at the SOBO Art Gallery for the whole family. 

160 West Plant Street, Winter Garden, FL 34787

Built in 1935, the Garden Theatre in Winter Garden used to be a gathering place for locals to watch the latest newsreels and films of the day. It is now a historic treasure that has grown into an extensive performing arts center where locals and visitors can come to see professional live theatre, concerts, dance, special events, and movies!

You can also learn all about and participate in their thrilling year-round arts education program. Head to the Garden Theatre for wonderful entertainment and a chance to support your local arts community members!

Winter Garden Events

Winter Garden is always hosting all sorts of events that you and your family will absolutely adore! Whether it’s the farmer’s markets, play, Halloweenfest, or the Christmas Parade, there’s inevitably something fun going on in this beautiful, historic neighborhood in Orlando.

The best way to stay up to date with events happening in Winter Garden is to download the UNATION App. We’ll provide all the details you need for upcoming fun stuff to do in Winter Garden!

If you decide to stop by and try any of these awesome places in Winter Garden, be sure to tag us in your photos on Instagram and let us know how you liked it! Don’t forget to use our hashtag #StuffToDoInOrlando as well so we can repost you.

We hope you enjoy these locations as much as we do, and have fun discovering new parts of Orlando!

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Katie Schwartz

Katie Schwartz

Katie is the City Manager for UNATION and author of the  Stuff to Do in Orlando blog. For more insight on the best events and things to do in the Orlando area, download the UNATION app and follow @StufftoDoinOrlando on Instagram and Facebook.

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