All Live Music & Nightlife in Winter Haven

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

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Peace Train Karaoke at Jessie’s Lounge - August 20, 2026

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No Reviews
August 20, 2026, 9:00 pm
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11:59 pm
Join Peace Train Karaoke every Thursday at 9 PM at Jessie’s Lounge in Downtown Winter Haven. Sing your favorite songs, enjoy the music, and explore the bar’s drink selection. Official event details: https://jessieslive.com/events Read more...
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The Jam with No Name at Jessie’s Lounge - August 26, 2026

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No Reviews
August 26, 2026, 7:00 pm
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11:59 pm
Every Wednesday at 7 PM, The Jam with No Name—hosted by Frankie—welcomes musicians of all skill levels to perform at Jessie’s Lounge in Downtown Winter Haven. Bring an instrument, share your talent, or come enjoy live music and drinks. Official event details: https://jessieslive.com/events Read more...
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Peace Train Karaoke at Jessie’s Lounge - August 27, 2026

New
No Reviews
August 27, 2026, 9:00 pm
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11:59 pm
Join Peace Train Karaoke every Thursday at 9 PM at Jessie’s Lounge in Downtown Winter Haven. Sing your favorite songs, enjoy the music, and explore the bar’s drink selection. Official event details: https://jessieslive.com/events Read more...
theatre winter haven

Live & Loud at the Ritz

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No Reviews
September 4, 2026, 6:00 pm
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11:00 pm
Live & Loud is Polk County’s monthly showcase of rising bands and local creative talent. The September lineup features 69 Fingers from Orlando, Ciquet from Lakeland, Lot Lizards from Tampa, and an additional act to be announced. Produced with Punk Kid Productions LLC. Official details and tickets: https://theatrewinterhaven.com/event/live-loud-at-the-ritz-8/ Read more...