Darren Dowling
📅 September 20 – October 5, 2025
⏰ 5:30 PM
📍 Calusa Brewing, Sarasota, FL
Raise a glass and celebrate the return of Oktoberfest at Calusa Brewing! This annual Sarasota tradition brings Bavarian vibes with craft beer, live music, and delicious food. From festive brews to pretzels and bratwurst, it’s the perfect way to kick off fall with family and friends.
👉 Why go? Enjoy seasonal craft beers, German-inspired bites, and a lively atmosphere that captures the spirit of Oktoberfest right here in Sarasota.
📅 September 20, 2025
⏰ 12 PM – 9 PM
📍 Fishermen’s Village, Punta Gorda, FL
Get ready for a day filled with tropical flavors and waterfront views at the Key Lime and Tropical Fest in Punta Gorda’s Fishermen’s Village. This one-day event is a celebration of Florida’s favorite citrus and island lifestyle, featuring tropical drinks, key lime pies, live entertainment, and local vendors.
👉 Why go? From refreshing cocktails to tropical treats, it’s the ultimate way to soak in Punta Gorda’s coastal charm while enjoying fun activities and live music.
📅 September 19, 2025
⏰ 6 PM – 9 PM
📍 Loaded Cannon Distillery, Bradenton, FL
Ahoy, mateys! Celebrate Talk Like a Pirate Day at Loaded Cannon Distillery in Bradenton. Dress in your best pirate gear, enjoy handcrafted spirits, and join in on pirate-themed fun and games. With rum at the heart of the celebration, this event is perfect for those looking for a playful night out.
👉 Why go? It’s a unique way to experience Bradenton’s craft distillery scene while letting your inner pirate come out to play.
From pirate fun in Bradenton to tropical flavors in Punta Gorda and Oktoberfest celebrations in Sarasota, September offers a lineup of events that showcase the best of Southwest Florida’s culture and community. Whether you’re local or visiting, these festivals are a great way to enjoy live entertainment, local flavors, and unforgettable experiences.
✨ Don’t miss out—grab your friends and family, and explore what Sarasota, Bradenton, and Punta Gorda have to offer this fall!
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