Best Bars in Winter Garden – Breweries and Wineries

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Lets raise our glasses and cheers to Winter Garden’s raveworthy bar scene. From lively outdoor breweries to rolling-hill wineries, this Orlando suburb has some of the best options for beer, wine, and craft cocktail lovers. And being just a short trip from the Downtown Orlando area, it’s the ideal spot to grab a drink with friends. 

To help narrow down your options, we’ve brewed up the ultimate beer and wine lover’s guide to the best bars in Winter Garden. 

Best Bars in Winter Garden - Breweries

Best Bars In Winter Garden Breweries And Wineries Best Bars In Winter Garden - Breweries And Wineries 2022

Crooked Can Brewing Company

Driving into Winter Garden, it’s hard to miss the Crooked Can Brewery. This local favorite is known for its free spirit, laid-back approach to beer making, excellent taste, and unmatched quality. Grab a seat inside or soak up the sunshine on their outdoor patio while sipping on their classics like the cloud chaser and the high stepper.

The best part? It’s located inside the Plant St. Market, so you have plenty of restaurant options to choose from. From pizza to sushi and everything in between—this market is packed with foods that pair perfectly with an ice-cold beer.

Monday| 11AM—11PM
Tuesday| 11AM—11PM
Wednesday| 11AM—11PM
Thursday | 11AM—11PM
Friday | 11AM—12PM
Saturday | 11AM—12PM
Sunday | 11AM—11PM

📍426 W. Plant St. Winter Garden, FL 34787

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Toll Road Brewing Company

Want to drink like a local? Off the beaten path, just a short drive out of Winter Garden, you’ll find Toll Road Brewing Company—named after the infamous Florida toll roads. This local-favorite brewery is a small craft brewery that specializes in craft beer made in-house, as well as showcasing other local Orlando breweries.

If you want to show some local love, we recommend hitting up this hidden gem on Tuesdays from 5 PM—7 PM for their happy hour to score $1 off pints and glasses of wine.

Monday | Closed
Tuesday | 5PM—9PM
Wednesday | 5PM—9PM
Thursday | 5PM—9PM
Friday | 4PM—11PM
Saturday | 12PM—11PM
Sunday | 1PM—6PM

📍101 W. McKey St. Ocoee, FL 34761

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Regency Beer, Wine, Liquor

When you don’t feel like grabbing a seat at an everyday bar, the Regency Beer, Wine, and Liquor store is here. But it isn’t your average liquor store. Not only do they have an incredible selection of beers and wines for you to take home. They also offer in-house tastings for you to enjoy during your shopping experience.

The best part? If you don’t feel like leaving the couch, they can also deliver alcohol nationwide right to your door.

Monday | 10AM—12AM
Tuesday | 10AM—12AM
Wednesday | 10AM—12AM
Thursday | 10AM—12AM
Friday | 10AM—12AM
Saturday | 10AM—12AM
Sunday | 10AM-10PM

📍16100 Marsh Rd. Suite 201 Winter Garden, FL 34787

Best Bars in Winter Garden - Wineries

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Whether you’re in search of the perfect date spot or a place to spend an afternoon with your crew, Winter Garden’s Attic Door should be at the top of your list. This swanky wine bar, bistro, and live music venue serves up unique wines, craft beers, and great bites.

The Attic Door also has happy hour every day from 4 PM—7 PM, as well as ladies’ night on Thursdays with $2 off wine glasses and $1 of beers. Grab your friends and explore the Historic downtown Winter Garden.

Monday | Closed
Tuesday | 4PM-10PM
Wednesday | 4PM-10PM
Thursday | 4PM-10PM
Friday | 4PM-11PM
Saturday | 4PM-11PM
Sunday | Closed

📍28 W. Plant St. Winter Garden, FL 34787

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Lakeridge Winery & Vineyards

Being Florida’s largest winery, Lakeridge Winery & Vineyards is an Orlando must-visit for locals and tourists. Located in Clermont, you’ll find 127 acres of rolling hills covered in Muscadine grapes—the same grapes used to create the award-winning wines you can taste or purchase in their gift shop. 

Lakeridge Winery also offers complimentary wine tours and tastings every day of the week, where you can sample their different seasonal wines. And during the summer months, they have Weekends at the Winery, which include live music and specialty offerings of food and wine! 

Monday | 10AM-5PM
Tuesday | 10AM-5PM
Wednesday | 10AM-5PM
Thursday | 10AM-5PM
Friday | 10AM-5PM
Saturday | 10AM-5PM
Sunday | 11AM-5PM

📍19239 US 27 North Clermont, FL 34715

Did We Miss Your Favorite Bar in Winter Garden?

Did we miss your favorite Winter Garden bars? Let us know by following us on Instagram at @StuffToDoInOrlando and tagging us in the bars, breweries, and wineries near Winter Garden that we should add to our next round-up. 

Kailey Boyer

Kailey Boyer

Kailey Boyer is an Arizona native, currently living her best life in Orlando, Florida. She’s passionate about hunting down and sharing all things her beautiful city has to offer. Making the hidden Florida gems accessible to everyone! You can find her exploring Orlando with a camera in hand, typing away in a local coffee shop, or in a packed car heading to the beach.