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Best Happy Hours in Winter Garden

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Happy Hour is the best hour and we’re here to celebrate the happiest hours in Winter Garden! We’ve gathered a list of some of the best happy hour locations in the area that are perfect for date night, girls night out, and more. From margaritas to wine and everything in between, Winter Garden has it all and you will too with our list of best happy hours in Winter Garden!

Double the margs, double the fun, right? That’s the motto here at the Whole Enchilada! Located in the heart of downtown Winter Garden, The Whole Enchilada offers a weekday happy hour with 2 for 1 margaritas from 4PM-7PM…as if we needed an excuse to drink more margaritas.

The Whole Enchilada also has a Taco Tuesday special which includes 2 tacos, chips and salsa, as well as a Mexican beer or beverage for $6.99. Don’t forget to check out their brunch menu on Sundays from 11AM-3PM with bottomless brunch cocktails!

Happy Hour: Monday-Friday | 4PM-7PM

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

Urban Flats is a creative and inspired American restaurant that is mixing the old with the new! They only use the freshest ingredients and are happy to serve you and your friends some of their amazing craft cocktails, beer, and wine from their extensive collection.

Happy Hour starts at 3:30PM on weekdays and ends at 7PM, but they also offer an all-day happy hour on the weekends! Enjoy $3 off specialty cocktails like their “Bacon Bourbon New Fashion” or “Here Today Pom Tomorrow,”  or enjoy $2 wine and $1 off beer.

Happy Hour: Monday-Friday | 3:30PM-7PM Saturday-Sunday | All Day

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

Martinis, mixology, music, and more. That’s what you’ll find at Pilars Martini and Pilars Loft in Winter Garden! Pilars is a great place to enjoy a perfectly crafted cocktail or martini with friends and munch on food from Market to Table right next door. Pilars is also located right next to the Garden Theatre and offers live music Thursday-Sundays.

Pilars features house-made bitters, simple syrups, and shrubs, and offers options like their cucumber cosmo, key lime martini, or tequila weekend. They also have an extensive wine and beer list for those craving something a little more classic.

Happy Hour:
Daily | 5PM-7PM
Extra Happy:
Saturday-Sunday | 3PM-5PM
Late Night:
Monday-Tuesday | 9PM-Close

📍146 W. Plant St. Suite 120 Winter Garden, FL 34787

The MoonCricket Grille is another staple in Winter Garden. Located right on Plant Street, this historic building has been around since 1912. MoonCricket Grille is a fun and hoppin’ place to come enjoy a beer or two during one of their BOGO happy hours on Tuesdays and Thursday.

MoonCricket is famous for their 99 beer club, where you can earn a T-shirt and your name on the wall for trying all 99 of their beers. Yes, you read that correctly, 99 beers! Come out and try them all during happy hour and enjoy some live music and a warm atmosphere.

Happy Hour:
Tuesday | BOGO Beer & Wine 11:30AM-8PM
Thursday | BOGO Beer 11:30AM-8PM

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

Nothing screams happy hour like $6 specialty drinks and $12 beer buckets! The Big Easy located in Winter Garden offers happy hour specials every day from 3PM-7PM, and even an all-day happy hour on Sunday! Not only do they have amazing drink options, but they also have a happy hour food menu with $6 bar bites like cajun shrimp, cheese stix, baked pretzels, and more.

The Big Easy is Winter Garden’s only New Orleans restaurant serving up delicious Louisiana classics like PO boys, shrimp and grits, and jambalaya. Be sure to check out their cocktail menu featuring hurricanes, margaritas, and frozen coladas. 

Happy Hour:
Monday-Saturday | 3PM-7PM
Sunday | All Day

📍15502 StoneyBrook W. Pkwy. Suite 118 Winter Garden, FL 34787

The Attic Door is a hidden gem in Winter Garden that is a swanky little wine bar and bistro. With amazing options like deviled eggs, cheese and charcuterie, and meatball sliders, you can enjoy bites while watching live music almost every night! 

Enjoy happy hour specials every day from 4PM-7PM with $2 off wines and $1 off beer, not to mention Tuesday nights where happy hour lasts all night long! They also have ladies’ night on Thursdays with even more drink specials from 4PM-10PM. It’s all right here at the Attic Door in Winter Garden.

Happy Hour: Monday-Sunday | 4PM-7PM

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

Just outside of Winter Garden you’ll find RusTeak, a restaurant that boasts handcrafted sandwiches, burgers, flatbreads, steaks, seafood, and pasta. The owners of RusTeak have built quite an empire in Orlando with the Stubborn Mule, Menagerie, and Feather and Quill Windermere. 

RusTeak also has an extensive cocktail menu and happy hour specials twice a day! Enjoy handcrafted cocktails like the 500 Days of Summer Mule, the Elder Wand, or the Orange Blossom Highball. Don’t forget to also check out their extensive list of beer and wine!

Happy Hour:
Monday-Sunday | 4PM-7PM & 10PM-11PM

📍1568 Maguire Rd. Ocoee, FL 34761

Ready to Enjoy the Best Happy Hours in Winter Garden? Follow us on Instagram for More!

Love happy hour? Follow us @StuffToDoInOrlando and tag us in happy hour pictures! Then, stick around for more great tips on the best things to do in the Orlando area.

Kimberly Gooch

Kimberly Gooch

Hi I'm Kim! I am a Florida native from Clearwater Florida, and now currently living in Orlando. I've been in Orlando for the last 6 years and love to explore everything the city has to offer. I travel a lot on the weekends visiting new cities, and in my spare time I enjoy hiking, biking, kayaking, and discovering new things to do.

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