Nightlife & Lounges

Crooked Can Brewing Company is a craft brewery and lively taproom located in historic Downtown Winter Garden at the heart of the vibrant Plant Street Market. Known for its bold, locally brewed beers and welcoming atmosphere, Crooked Can offers an authentic Central Florida craft beer experience that appeals to both seasoned beer enthusiasts and casual visitors. From rotating seasonal brews and classic styles to limited-edition batches, there’s a perfect pour for every palate. Pair your favorite craft beer with delicious bites from the on-site food vendors, relax on the spacious patio with friends, or join in one of the regular live music events and community gatherings hosted here. Add Crooked Can Brewing Company to your must-visit list and plan your visit for great brews, bites, and good vibes!

Fridays on the Plaza brings live music to historic Downtown Winter Garden every Friday evening at the Centennial Plaza Gazebo. From 7:00 PM to 9:00 PM, local musicians perform free, family-friendly sets spanning jazz, blues, pop, country, rock, and more, creating an inviting atmosphere in the heart of the city. The event pairs perfectly with Winter Garden’s walkable streets, nearby shops, and popular restaurants, making it easy to stroll, dine, sip, and relax while enjoying the music. Talented performers set the tone for a laid-back yet lively evening, turning the plaza into a welcoming gathering place for the community. Whether you plan a date night, meet friends, or enjoy a casual outing, Fridays on the Plaza offers a vibrant local experience that kicks off the weekend on a high note. Add Fridays on the Plaza to your event calendar and plan your visit this Friday!

Windermere Brewing Company is a craft brewery and welcoming taproom nestled in charming Historic Windermere, Florida. With a rotating lineup of house-brewed beers — from crisp lagers and smooth ales to bold IPAs and seasonal specialties — this casual local favorite blends quality brewing with a laid-back social atmosphere perfect for casual hangouts, weekend afternoons, or lively evenings with friends. Enjoy indoor seating or relax on the outdoor patio while pairing fresh pours with rotating food trucks, trivia nights, live music, and community events. Add it to your must-visit spots and stop by for a flight of craft brews.