Share on facebook
Share on twitter
Share on linkedin
Share on pinterest

Best Bars in Winter Garden – Breweries and Wineries

A Story By

More beer and wine, please! Orlando is full of breweries and wineries, and this time we’re heading out to Winter Garden to find the best place to grab a drink with friends.

Winter Garden is just a hop, skip, and a jump away from downtown Orlando, and is not too far from wine country out in Lake County. It’s the best of both worlds when looking for the Best Bars in Winter Garden!

Best Bars in Winter Garden - Breweries

Crooked Can Brewery is the place in Winter Garden where everyone knows your name. Located right in the heart of the Plant St. Market, Crooked Can offers a free spirit, laid-back approach to beer making, but with excellent taste and unmatched quality. Grab your friends and head to this brewery to enjoy classics like the cloud chaser, high stepper, and more.

This brewery has an onsite taproom that offers tours throughout the week and is located in the Plant St. Co-Op Market so you have plenty of options to choose from for food. Be sure to stay in touch with their social media, as they are always hosting fun events!

Monday-Thursday | 11AM-11PM
Friday-Saturday | 11AM-12PM
Sunday | 11AM-11PM

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

Just a short drive out from Winter Garden you’ll find Toll Road Brewing Company in Ocoee! Toll Road Brewing Company was named after, you guessed it, toll roads that are inevitable all over Central Florida. This brewery is a small craft brewery that specializes in delicious craft beer made in-house, as well as showcases other local Orlando breweries. 

Aside from their core beers, rotating beers, and specialty brews, you can also enjoy Sunday Funday at Toll Road with bottomless mimosas and tasty treats. They also have happy hour on Tuesdays from 5PM-7PM with $1 off pints and glasses of wine. 

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

📍101 W. McKey St. Ocoee, FL 34761

Regency Beer, Wine, and Liquor isn’t your average liquor store. Not only do they have an incredible selection of beers and wines for you to take home, but they also have tastings for you to come in and enjoy some of their amazing specials and beer selections.

If Regency Beer, Wine, and Liquor doesn’t have what you want, they will make sure to call and order it for you! They can also deliver alcohol nationwide right to your door! Check out their taproom to try local Orlando breweries, and bring home cans and growlers to enjoy at home.

Monday-Saturday | 10AM-12PM
Sunday | 10AM-10PM

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

Best Bars in Winter Garden - Wineries

Looking for the perfect place to spend an afternoon in Winter Garden? Check out the Attic Door, a swanky little wine bar, bistro, and live music venue. Here you can find unique wines, craft beers,  and great bites. They also have a tea room experience that is available on select weekends!

The Attic Door also has happy hour every day from 4PM-7PM, as well as ladies’ night on Thursdays with $2 off wine glasses and $1 of beers. Grab your friends and explore Historic downtown Winter Garden, and don’t forget to check out the Attic Door for all your beer and wine needs!

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

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

Not too far out from Winter Garden is Lakeridge Winery & Vineyards! Located in Clermont, this is Florida’s largest winery, producing award-winning, Muscadine-grape wines to send to all over Central Florida. With 127 acres of vineyards and a tasting room/shop, it’s the perfect place to spend a day in Central Florida enjoying authentic Florida wine. 

Lakeridge Winery also offers complimentary wine tours and tastings 7 days a week where you can sample their different seasonal wines. During the summer months, they have Weekends at the Winery which includes live music and specialty offerings of food and wine!

Monday-Saturday | 10AM-5PM
Sunday | 11AM-5PM

📍19239 US 27 North Clermont, FL 34715

Hang on to your wine glasses, there’s another winery near Orlando! Hutchinson Farm Winery in Apopka Florida is a small boutique winery that is family-owned and operated by John and Sherry Hutchinson. It is one of the smallest Florida wineries that produces local and hand-made wine.

Not only is Hutchinson Farm Winery a local winery, but they also are a member of Fresh From Florida so you know their grapes are going to be good. They also partner with local blueberry farmers around town for their famous blueberry wine, and are happy to support other local Orlando farmers!

Monday-Thursday | Closed
Friday-Sunday | 12PM-5PM

📍8061 Stone Road Apopka, FL 32703

Enjoyed the Best Bars in Winter Garden? Follow Us on Instagram!

Beer and Wine have us feelin’ fine! Check out our favorite bars, breweries, and wineries near Winter Garden, then don’t forget to follow us @StuffToDoInOrlando and tag us in your pictures when you visit!

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.

Subscribe Now

Get the best things to do in Orlando delivered right to your phone! 
Please enter a valid email address.
Thank you for subscribing!
Weekend Guides
Checkout all the past Tampa Bay weekly Guides in the Stuff To Do Archive
Find Stuff To Do
Discover the best featured and staff pick events in Tampa Bay on UNATION
Connect on Facebook
Join our Stuff to Do in Tampa Bay Facebook group to find more upcoming events

Get the App!

Download the UNATION app and discover tons of local events


Share on facebook
Share on twitter
Share on pinterest
Share on linkedin


Share on facebook
Share on twitter
Share on pinterest
Share on linkedin


Share on facebook
Share on twitter
Share on pinterest
Share on linkedin