All Events

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Winter Haven Coffee, Tea, and Dessert Tour - November 11, 2026

No Reviews
November 11, 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 - November 11, 2026

No Reviews
November 11, 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 - November 11, 2026

No Reviews
November 11, 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 - November 12, 2026

No Reviews
November 12, 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 - November 12, 2026

No Reviews
November 12, 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 - November 12, 2026

No Reviews
November 12, 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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DJ Trinidad - November 12, 2026

No Reviews
November 12, 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 - November 13, 2026

No Reviews
November 13, 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 - November 13, 2026

No Reviews
November 13, 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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Wine, Chocolate, and Cheese

No Reviews
November 13, 2026, 5:30 pm
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8:30 pm
Main Street Winter Haven’s 10th Annual Wine, Chocolate & Cheese event invites guests to sample curated wine-and-chocolate or wine-and-cheese pairings at more than 40 Downtown Winter Haven businesses. This map-based tasting event encourages attendees to explore and shop local downtown businesses. Official event details: https://www.mainstreetwh.com/event/wcc2026/ Read more...