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Live Music in Winter Haven: Where to Catch Live Entertainment Over the Next Week

Music lovers will have several opportunities to enjoy live entertainment around Winter Haven over the next week, with local musicians taking the stage at area bars and restaurants.

Whether you’re looking for an evening out during the week or some live music to enjoy over the weekend, there are several performances to add to your calendar.

Here’s where you can catch live music:

Thursday

  • Chase Dixon will perform at Cypresswood Pub from 6 to 9 p.m.
Poster for Cypresswood Pub announcing dinner specials, live music schedule, soups of the day with prices, and November 12–14 dinner hours 5pm–9pm.

Friday

  • TMike & Duke Burr will take the stage at The Twisted Prop from 6 to 9:30 p.m.

Saturday

  • Jaded will perform at Tanner’s Lakeside from 7 to 10 p.m.

Sunday

  • Acoustic Roots will perform at Tanner’s Lakeside from 2 to 6 p.m.
November 2026 events calendar for Tanners Lakeside, with a left info panel and a daily grid listing bingo, live music, and specials.

Next Wednesday

  • Sidd & Duke will perform at Somewhere Sports Bar from 6:30 to 9:30 p.m.

From weekday performances to weekend entertainment, there’s no shortage of opportunities to support local musicians and enjoy live music around the Winter Haven area.

Close-up of an acoustic guitar against a textured dark backdrop with bold 'Live Music' script and a white circular logo in the lower-right corner.
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Allison

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