All Events

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Winter Haven Happy Hour Walking Tour

Winter Haven Happy Hour Pub Crawl - September 16, 2026

New
No Reviews
September 16, 2026, 4:30 pm
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7:30 pm
Price: $157
Experience Winter Haven’s local nightlife on a guided happy-hour pub crawl featuring drinks, food, and entertaining local stories. Schedule: Wednesdays and Fridays, 4:30–7:30 p.m. Exact meeting and parking instructions are provided with your booking. Guests must meet the tour’s age requirements. View full tour details and book now. Read more...
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Karaoke Tuesdays At Tipsy Hen - September 16, 2026

New
No Reviews
September 16, 2026, 7:00 pm
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10:00 pm
Karaoke at Tipsy Hen every Tuesday with Castle Karaoke (Brooke & Alden) 7-10pm. Family friendly and a fun supportive atmosphere to sing your hearts out every week while enjoying dinner and drinks! Read more...
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Flavors of Winter Haven Food Tour - September 17, 2026

New
No Reviews
September 17, 2026, 2:00 pm
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5:00 pm
Price: $124
Discover the flavors, history, and locally owned restaurants of downtown Winter Haven on this guided culinary walking tour. Schedule: Tuesdays, Thursdays, and Saturdays, 2:00–5:00 p.m. All featured tastings are included. Exact meeting and parking instructions are provided with your booking. View full tour details and book now. Read more...
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Winter Haven Chef’s Table Experience - September 17, 2026

New
No Reviews
September 17, 2026, 5:00 pm
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8:00 pm
Price: $250
Enjoy an elevated guided dining experience showcasing Winter Haven chefs, restaurants, and thoughtfully prepared courses. Schedule: Thursdays and Saturdays, 5:00–8:00 p.m. Exact meeting and parking instructions are provided with your booking. Minimum guest requirements may apply. View full tour details and book now. Read more...
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Happy Hour Trivia Show - September 17, 2026

New
No Reviews
September 17, 2026, 6:00 pm
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11:00 pm
WEDNESDAYs: 🐪🥃 ▫️Trivia 6pm! ▫️Enjoy a BOGO 8pm-12am! (Like & show post to bartender) ▫️$6 VG Caramel Vodka Espresso Martinis (Mon-Thur / 6pm-9pm) ALL DAY ER-DAY DEALS: 💲 ▫️$2 Twin P Whiskey ▫️$3 Bushmills Irish Whiskey HAPPY HOUR: 🍸🍷🥂🥃 ▫️$3 off Wells & Wines ▫️$2 off Beers – Sunday & Monday! (ALL DAY) – Tuesday-Thursday! (12pm-6pm) – Friday & Saturday! Read more...
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The Bucket List!

New
No Reviews
September 17, 2026, 8:00 pm
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10:00 pm
Price: $10
Audience suggestions are pulled from a bucket and turned into jokes on the spot in this fast-paced improvised comedy show with no scripts and no safety net. Doors open at 7 PM and the show starts at 8 PM. Ages 21 and older. Two-item minimum per person. Tickets start at $10. Present your confirmation email or QR code for admission Read more...
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DJ Trinidad - September 17, 2026

New
No Reviews
September 17, 2026, 9:00 pm
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2:00 am
DJ Trinidad typically spins music out back on the patio Read more...
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Winter Haven Coffee, Tea, and Dessert Tour - September 18, 2026

New
No Reviews
September 18, 2026, 10:00 am
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3:00 pm
Price: $125
Join us on a sweet and savory journey through Winter Haven’s local coffee shops and dessert destinations. Enjoy coffee, tea, pastries, desserts, local stories, and a guided walking experience. Schedule: Mondays, Wednesdays, and Fridays, 10:00 a.m.–3:00 p.m. All tastings are included. Exact meeting and parking instructions are provided with your booking. View full tour details and book now. Read more...
Winter Haven Happy Hour Walking Tour

Winter Haven Happy Hour Pub Crawl - September 18, 2026

New
No Reviews
September 18, 2026, 4:30 pm
-
7:30 pm
Price: $157
Experience Winter Haven’s local nightlife on a guided happy-hour pub crawl featuring drinks, food, and entertaining local stories. Schedule: Wednesdays and Fridays, 4:30–7:30 p.m. Exact meeting and parking instructions are provided with your booking. Guests must meet the tour’s age requirements. View full tour details and book now. Read more...
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Jerry Wayne Longmire from The Reckon Yard Podcast!

New
No Reviews
September 18, 2026, 8:00 pm
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September 19, 2026, 10:00 pm
Price: $30
Jerry Wayne Longmire, known from The Reckon Yard podcast and the viral Truck Astrology series, performs live for two nights. Doors open at 7 PM and the show starts at 8 PM. Ages 21 and older. Two-item minimum per person. Tickets start at $30. Present your confirmation email or QR code for admission and arrive at least 30 minutes before Read more...