Entertainment events in Winter Haven

• Fri, 06 Feb, 2026 - 08:00 PM

  Kevin Farley: Yes THAT Farley!

  19 3rd St NW

  USD 30
• Fri, 09 Jan, 2026 - 08:00 PM

  Renard Hirsch from Nateland Presents!

  19 3rd St NW

  USD 20
• Fri, 23 Jan, 2026 - 05:30 PM

  Cordero Music Presents Youth Music Night

  Bowen Yard

  Free
• Fri, 02 Jan, 2026 - 05:00 PM

  First Friday Winter Haven

  Downtown Winter Haven Historic District

  164+ Interested
• Thu, 08 Jan, 2026 - 08:00 PM

  Rob Smiles & Friends!

  19 3rd St NW

  USD 8
• Fri, 16 Jan, 2026 - 08:00 PM

  Rob Little: MAXIM Comedian of the Year!

  19 3rd St NW

  USD 25
• Sun, 04 Jan, 2026 - 03:00 PM

  It's A Twizted Party!

  Caribbean Bay

  50+ Interested
• Fri, 23 Jan, 2026 - 08:00 PM

  Patrick Garrity: The Never Ending Tour!

  19 3rd St NW

  USD 20
• Fri, 23 Jan, 2026 - 07:00 PM

  Shades of HUNKS at The Ritz Theatre (Winter Haven, FL) 01/23/26

  Historic Ritz Theatre, Inc

  USD 19
• Tue, 14 Apr, 2026 - 07:00 PM

  Rock of ABBA at The Historic Ritz Theater Winter Haven, Fl

  Ritz Theatre

  6+ Interested
• Thu, 05 Feb, 2026 - 08:00 PM

  Peter Antoniou: Psychic Comedian!

  19 3rd St NW

  USD 30
• Fri, 16 Jan, 2026 - 06:00 PM

  Monsters Wrestling Orlando – Men’s Championship Tournament at Tanners Lakeside

  1006 S Lake Howard Dr, Winter Haven, FL, United States, Florida 33880

  16+ Interested
• Thu, 12 Feb, 2026 - 08:00 PM

  Mark Christopher & Friends!

  19 3rd St NW

  USD 15
• Fri, 27 Mar, 2026 - 07:30 PM

  The Unteachables Comedy Tour!

  19 3rd St NW

  USD 25
• Fri, 20 Feb, 2026 - 07:00 PM

  Light Up The Night 5k Winter Haven

  250 Magnolia Avenue Southwest Winter Haven, Florida

  192+ Interested