Live Music Around Winter Haven This Weekend: June 26-28
Looking for live music this weekend in the Winter Haven area? From classic rock and country favorites to karaoke and acoustic performances, there are plenty of opportunities to enjoy great local entertainment.
Cypresswood Pub
Cypresswood Pub has a full weekend lineup planned:
- Thursday: DJ Steve & Karaoke from 6:00 p.m. to 9:00 p.m.
- Friday: 99 in the Shade from 6:00 p.m. to 9:00 p.m.
- Saturday: The Grateful Alive takes the stage.

Tanner’s Lakeside
Head to Tanner’s Lakeside for live music all weekend long:
- Friday: Whiskey Whisper from 7:00 p.m. to 10:00 p.m.
- Saturday: Jaded from 7:00 p.m. to 10:00 p.m.
- Sunday: Sgt. Shredder from 2:00 p.m. to 6:00 p.m.
VFW Winter Haven
Catch B. Haven performing at the VFW in Winter Haven on Saturday, from 6:00 p.m. to 9:00 p.m.
Port 27
Enjoy an afternoon of live music on Sunday with the Joey Foley Duo featuring Renee Riddle at Port 27 from 4:00 p.m. to 7:00 p.m.
Be sure to check out the Tipsy Hen calendar below as well!

Whether you’re looking for a fun karaoke night, a relaxing lakeside concert, or an afternoon of acoustic music, there’s something happening around Winter Haven this weekend.
Want Your Music Featured?
Musicians performing in the Winter Haven area who would like their shows included in a future roundup can submit their schedules to [email protected]. Be sure to include “LIVE MUSIC” in the subject line to be featured in an upcoming edition of the Winter Haven Daily music listings.


