All Live Music & Nightlife in Winter Haven

Concerts, live music, karaoke, trivia, comedy, and evening entertainment.

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Karaoke Tuesdays At Tipsy Hen - October 28, 2026

New
No Reviews
October 28, 2026, 7:00 pm
-
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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Happy Hour Trivia Show - October 29, 2026

New
No Reviews
October 29, 2026, 6:00 pm
-
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 - October 29, 2026

New
No Reviews
October 29, 2026, 9:00 pm
-
2:00 am
DJ Trinidad typically spins music out back on the patio Read more...
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Karaoke Tuesdays At Tipsy Hen - November 4, 2026

New
No Reviews
November 4, 2026, 7:00 pm
-
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...
happy hour trivia show at barrel 239 768x1017

Happy Hour Trivia Show - November 5, 2026

New
No Reviews
November 5, 2026, 6:00 pm
-
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 5, 2026

New
No Reviews
November 5, 2026, 9:00 pm
-
2:00 am
DJ Trinidad typically spins music out back on the patio Read more...
karaoke tuesdays at typsy hen 768x403

Karaoke Tuesdays At Tipsy Hen - November 11, 2026

New
No Reviews
November 11, 2026, 7:00 pm
-
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...
happy hour trivia show at barrel 239 768x1017

Happy Hour Trivia Show - November 12, 2026

New
No Reviews
November 12, 2026, 6:00 pm
-
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

New
No Reviews
November 12, 2026, 9:00 pm
-
2:00 am
DJ Trinidad typically spins music out back on the patio Read more...
karaoke tuesdays at typsy hen 768x403

Karaoke Tuesdays At Tipsy Hen - November 18, 2026

New
No Reviews
November 18, 2026, 7:00 pm
-
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...