Entertainment

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!

Winter Garden Music Festival is a vibrant, free annual outdoor music celebration in historic Downtown Winter Garden that brings together live performances, local dining, and community energy for an unforgettable day of entertainment. Featuring 30+ music acts performing across multiple stages throughout downtown, this festival offers a mix of genres — from rock and pop to blues, folk, jazz and Latin rhythms — so there’s something for every music lover. Expect food and drink vendors, artisan boutiques, and streets closed to cars so pedestrians can enjoy the lively festival atmosphere. Whether you’re planning a family outing, date day, or group adventure, Winter Garden Music Festival delivers a memorable cultural experience right in the heart of the city. Add the Winter Garden Music Festival to your events calendar and plan your visit for great music, food, and downtown fun!

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.

Located on the Rollins College campus, the Rollins Museum of Art is a free, year-round cultural destination featuring rotating exhibitions and a diverse collection spanning classical to contemporary works. With family-friendly programs, guided tours, and engaging events, it’s a must-visit spot for art lovers seeking culture and entertainment in the heart of Winter Park. Discover world-class art and engaging exhibitions at the Rollins Museum of Art.

A beloved annual tradition, the Winter Park Sidewalk Art Festival brings Central Park and Park Avenue to life with fine art from top juried artists, live music, and a lively outdoor atmosphere. Family-friendly and walkable, the festival also features interactive art activities for kids, making it a standout entertainment experience for art lovers of all ages in the heart of Winter Park. Discover featured artists, events, and festival details here.

A modern, family-friendly cultural hub in the heart of Winter Park, the Library & Events Center offers live performances, community events, and interactive programs for all ages. With open green spaces, kid-friendly activities, and a scenic park and lake setting, it’s an ideal spot for families to enjoy arts, entertainment, and quality time together. Click here to explore events, programs, and experiences for all ages.