Winter Garden Bars

Sun, Nov 12, 2023 at 4:35AM

Winter Garden Bars

Top Winter Garden Bars: Where to Enjoy Drinks and Entertainment in Orlando

Welcome to Winter Garden, Florida, a charming city full of character, warmth, and a thriving bar scene! In this lively enclave, you’ll find an array of winter garden bars offering everything from craft beers and sophisticated wine selections to creative cocktails and family-friendly treats. So, get ready to embark on a tantalizing journey through Winter Garden’s vibrant winter garden bars scene, where drinks and entertainment await you at every turn.

Downtown Winter Garden FL  Winter Garden FL Restaurants

Key Takeaways

  • Explore Winter Garden’s craft beer havens, wine bars & lounges, live music venues and outdoor patios for drinks and entertainment.

  • Discover unique cocktail experiences at Pilars Martini Bar or Urban on Plant Kitchen & Bar.

  • Enjoy family friendly spots like BurgerFi and Kelly’s Homemade Ice Cream or explore hidden gems like Regency Wine & Liquor!

Craft Beer Havens

Winter Garden is a paradise for craft beer enthusiasts, with numerous delightful breweries and bars offering a vast selection of beers to satisfy your taste buds. With an emphasis on atmosphere and variety, head to Crooked Can Brewing Company, Plant Street Market, and Miller’s Ale House for some of the best craft beers in town.

Crooked Can Brewing Company

Crooked Can Brewing Company, nestled in the heart of Winter Garden, is a treasure waiting to be discovered. This brewery boasts an impressive range of beers, including:

  • High Stepper American IPA

  • Florida Sunshine Lager

  • Cloud Chaser Hefeweizen

  • McSwagger’s Own Amber Ale

Plus, you’ll find seasonal offerings like Citrus Kicker.

Enjoy their outdoor patio and don’t miss out on the weekly brewery tours, where you get to witness the beer-making process from start to finish.

Plant Street Market

Plant Street Market, located in historic downtown Winter Garden, is a vibrant 12,000 square foot indoor artisan market. It offers local food, handcrafted items, and a selection of craft beers. Here, you’ll find Crooked Can Brewing Company’s exclusive range of craft beers, giving beer lovers a unique tasting experience.

With plenty of indoor and outdoor space for events, Plant St Market is a community food hub that offers something for everyone.

Miller's Ale House

Miller’s Ale House, with its vibrant sports bar atmosphere and wide assortment of craft beers, is a perfect spot for beer lovers. This popular Winter Garden bar boasts over 35 beers on tap, ensuring that there’s a brew for everyone to enjoy. With a wide variety of food options and daily specials, Miller’s Ale House is the perfect spot for beer enthusiasts to grab a bite and catch the game on one of their 60+ TVs.

Wine Bars & Lounges

Winter Garden’s wine bars and lounges are perfect venues for those seeking a refined evening. Indulge in a refined experience at The Attic Door, Pilar’s Martini Bar, and Urban Flats: Restaurant and Wine Bar, where you can sip on exquisite wines, craft beers, and expertly crafted cocktails in elegant surroundings.

The Attic Door

Located in Winter Garden, The Attic Door serves as a stylish live music venue and wine bar. Offering a variety of wines, craft beers, and cocktails, this cozy spot, located inside a charming building, features live music performances spanning genres like jazz, blues, and acoustic.

With over 25 wines available by the glass, The Attic Door is the perfect place to unwind and enjoy some soulful tunes in a relaxing atmosphere.

Pilar's Martini Bar

Pilar’s Martini Bar, a popular spot among both locals and tourists, offers exceptional martinis, innovative mixology, and live music performances. The cozy 30’s deco style and art-filled atmosphere make for a warm and welcoming setting to enjoy hand-mixed martinis and other delicious cocktails at one of the best bars in town.

With its impressive drinks menu and lively entertainment, Pilar’s Martini Bar is a must-visit in Winter Garden.

Urban Flats: Restaurant and Wine Bar

Urban Flats: Restaurant and Wine Bar in Winter Garden offers a refreshing and trendy dining experience. This cool spot offers a great selection of wines, craft beers, and cocktails, along with a diverse menu featuring American, Contemporary, and Fusion cuisine.

The restaurant’s modern decor is complemented by local photos of downtown Winter Garden, creating a cozy yet contemporary atmosphere that’s perfect for a night out with friends or a romantic date.

Live Music Venues

From Hagan O’Reilly’s Irish Pub and The Whole Enchilada Fresh Mexican Grill & Rooftop Bar to Rosallie Le French Cafe, Winter Garden boasts a thriving live music scene with a variety of musical experiences. From traditional Irish tunes to rooftop performances, there’s something for every music lover in Winter Garden.

Hagan O'Reilly's Irish Pub

Hagan O’Reilly’s Irish Pub in Winter Garden offers an authentic Irish pub experience. This popular spot not only offers a great selection of beers and traditional Irish grub but also features live music across various genres, including Irish tunes.

The welcoming atmosphere and lively entertainment make Hagan O’Reilly’s Irish Pub a must-visit destination for music enthusiasts.

The Whole Enchilada Fresh Mexican Grill & Rooftop Bar

The Whole Enchilada Fresh Mexican Grill & Rooftop Bar is the place to be if you’re in the mood for Mexican cuisine complemented by live music. This Winter Garden gem offers a fantastic rooftop setting where you can enjoy live music performances while savoring delicious Mexican dishes.

The lively atmosphere and mouthwatering food make this spot a perfect destination for a fun night out.

Rosallie Le French Cafe

Experience a taste of France in Winter Garden at Rosallie Le French Cafe. This charming cafe offers southern French cuisine and live jazz music on weekends, creating a delightful and relaxing atmosphere.

Immerse yourself in the authentic French ambiance while savoring delicious dishes and listening to soothing tunes.

Outdoor Patios & Scenic Spots

Relishing a drink and a meal in a stunning outdoor setting is an unmatched experience. Near Winter Garden, you’ll find several scenic outdoor patios and spots where you can relax and take in the picturesque surroundings.

Experience the beauty of Winter Garden at The Tasting Room At the Chef’s Table, The Hangry Bison, and The Exchange.

The Tasting Room At the Chef's Table

The Tasting Room At the Chef’s Table in Winter Garden offers a one-of-a-kind dining experience. With its intimate atmosphere, this charming spot offers stunning views of the culinary gardens and provides a private room for guests to enjoy a customized tasting menu.

Indulge in exquisite food and wine pairings while taking in the captivating scenery.

The Hangry Bison

Offering a range of gourmet burgers, bourbon, craft beer, and cocktails, The Hangry Bison is a bustling locale in Winter Garden. With its casual atmosphere and outdoor seating, it’s the perfect place to unwind with friends or family while enjoying some delicious food and drinks.

The Exchange

The Exchange, a vibrant mixed-use building filled with eateries and shops, is situated in the heart of downtown Winter Garden. The lively atmosphere makes it an ideal destination for a fun afternoon or evening out.

Enjoy the vibrant scene while sipping on a drink or grabbing a bite to eat.

Unique Cocktail Experiences

Winter Garden houses several bars in winter garden that serve creative and unique cocktails, certain to impress those seeking such an experience. Check out Pilars Martini, Urban on Plant Kitchen & Bar, and Mangoni Italian Market Pizza for innovative concoctions that will tantalize your taste buds and take your cocktail experience to new heights.

Pilars Martini

Known for its handcrafted cocktails and live music, Pilars Martini is a snug piano bar located in Winter Garden. Offering an extensive menu of hand-mixed martinis, this gem is the perfect spot to enjoy a delicious drink in a warm and inviting atmosphere.

The live music, ranging from jazz to contemporary tunes, adds to the unique charm of the favorite bar area.

Urban on Plant Kitchen & Bar

Offering a novel interpretation of cocktails, Urban on Plant Kitchen & Bar is a fashionable locale in Winter Garden. Their creative concoctions, using the freshest ingredients, will leave you craving more. Not only do they offer innovative drinks, but their food menu is equally impressive, featuring a mix of American and World cuisine.

Mangoni Italian Market Pizza

Mangoni Italian Market Pizza in Winter Garden adds an Italian flair to your cocktail experience. This charming spot offers Italian-style cocktails alongside their mouthwatering pizza and other Italian dishes.

The welcoming atmosphere makes it a perfect destination for a relaxed evening with friends or a romantic date night.

Family-Friendly Options

Offering several family-friendly dining options, Winter Garden is an ideal destination for families. Enjoy a fun and relaxed atmosphere at BurgerFi, Kelly’s Homemade Ice Cream, and Scoops Old Fashioned Ice Cream Store, where you’ll find delicious food and treats that will delight both kids and adults.


BurgerFi in Winter Garden provides a top-notch family-friendly dining experience. Offering a wide variety of delicious burgers, including the Beyond Burger for plant-based eaters, BurgerFi ensures that there’s something for everyone.

Their kids’ menu features options like Single Cheeseburger, Hot Dog, and Grilled Cheese, ensuring that even the pickiest of eaters will be satisfied.

Kelly's Homemade Ice Cream

Kelly’s Homemade Ice Cream in Winter Garden is the perfect spot to satiate your sugar cravings. This family-owned ice cream shop offers a wide range of popular flavors, such as Sweet Strawberry, Chocolate, and Ore-Dough.

The inviting atmosphere and delicious ice cream make Kelly’s a perfect destination for a family treat.

Scoops Old Fashioned Ice Cream Store

Scoops Old Fashioned Ice Cream Store in Winter Garden offers a range of unique ice cream flavors that are sure to delight the entire family. With flavors like Cotton Candy, Butter Pecan, and Chocolate Chip Cookie Dough, there’s something for everyone at this family-friendly ice cream store.

Hidden Gems

Winter Garden is brimming with undiscovered treasures. Venture off the beaten path and explore Regency Wine & Liquor, Sir Benji’s Donuts, and Schweini’s Delicatessen, where you’ll find unique offerings and experiences that are sure to make your visit to Winter Garden unforgettable.

Regency Wine & Liquor

Offering a wide array of:

  • wines

  • spirits

  • beers

  • mixers

  • cigars

Regency Wine & Liquor is a hidden gem in Winter Garden. With rare and unique items in their inventory, this wine and liquor store is a must-visit for those looking to discover something new and exciting.

Don’t miss their special events and tastings for an even more memorable experience.

Sir Benji's Donuts

Sir Benji’s Donuts, a must-visit hidden gem in Winter Garden, is the perfect destination for those with a sweet tooth. This family-owned donut shop offers a variety of unique donuts, such as Major Glazer, Churro Doughnut, and The French Quarter.

Satisfy your cravings and discover new favorites at this delightful donut shop.

Schweini's Delicatessen

Experience a slice of Germany in Winter Garden at Schweini’s Delicatessen. This family-run deli offers traditional German dishes with a modern twist, including bratwurst, schnitzel, and their signature Schweinibraten sandwich.

Experience authentic German cuisine and flavors at this hidden gem.


From craft beer havens and sophisticated wine bars to family-friendly spots and hidden gems, Winter Garden offers a diverse and exciting bar scene waiting to be explored. Discover the unique experiences and memorable moments that await you in this charming Florida city. Cheers to your Winter Garden adventure!

Frequently Asked Questions

What types of bars can I find in Winter Garden?

Head to Winter Garden to find craft beer havens, wine bars, live music venues and hidden gems - all within reach!

Are there any family-friendly dining options in Winter Garden?

Yes, Winter Garden has plenty of family-friendly dining options, such as BurgerFi, Kelly's Homemade Ice Cream, and Scoops Old Fashioned Ice Cream Store.

Can I find live music at any of the bars in Winter Garden?

Yes, you can find live music at The Attic Door, Pilar's Martini Bar, Hagan O'Reilly's Irish Pub, and Rosallie Le French Cafe in Winter Garden.

Are there any unique cocktail experiences in Winter Garden?

Experience a unique cocktail with Pilars Martini, Urban on Plant Kitchen & Bar, or Mangoni Italian Market Pizza in Winter Garden.

What are some hidden gems in Winter Garden?

Discover the hidden gems of Winter Garden - Regency Wine & Liquor, Sir Benji's Donuts, and Schweini's Delicatessen - for an unforgettable experience.

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