All Events

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Winter Haven Coffee, Tea, and Dessert Tour - September 9, 2026

New
No Reviews
September 9, 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 9, 2026

New
No Reviews
September 9, 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 9, 2026

New
No Reviews
September 9, 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 10, 2026

New
No Reviews
September 10, 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 10, 2026

New
No Reviews
September 10, 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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Ladies Night Self-Care Social

New
No Reviews
September 10, 2026, 5:30 pm
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8:30 pm
Price: $10
Before the holiday rush, take a night for yourself. Main Street Winter Haven invites you to join us for Ladies’ Night Self-Care Social, September 10th, 5:30-8:30 PM. Participating Downtown Winter Haven businesses will be open late for a fall night of shopping, Sipping, Pampering, and Socializing. We hope you will explore all that Downtown Winter Haven offers to help you Read more...
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Happy Hour Trivia Show - September 10, 2026

New
No Reviews
September 10, 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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Grove Roots Run Club - September 10, 2026

New
No Reviews
September 10, 2026, 6:30 pm
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8:00 pm
Run Club departs from Grove Roots Brewing Co. at 6:30 PM. All levels are welcome, with 1.5-mile and 3-mile route options. Enjoy a friendly downtown run followed by refreshments at the brewery. Official event details: https://groveroots.com/events/category/special-event/list/ Read more...
WH Food Tours Logo

Jander Gray & Friends!

New
No Reviews
September 10, 2026, 8:00 pm
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10:00 pm
Price: $15
Jander Gray brings his honest, sarcastic dad humor and carefree stage presence to Laugh Out Lounge with a lineup of funny friends. Doors open at 7 PM and the show starts at 8 PM. Ages 21 and older. Two-item minimum per person. Tickets start at $15. Present your confirmation email or QR code for admission and arrive at least 30 Read more...
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DJ Trinidad - September 10, 2026

New
No Reviews
September 10, 2026, 9:00 pm
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2:00 am
DJ Trinidad typically spins music out back on the patio Read more...