Upcoming Live Music Events

Battle of the Decades: Dueling Piano Show

 Ritz Theatre 4 Mar 2026
ENTERTAINMENT

The Blackwood Brothers Quartet in Winter Haven

 Westwood Bible Baptist Church - 3210 Avenue G NW 4 Feb 2026
ENTERTAINMENT

Karen Peck & New River in Winter Haven

 First Church Of God 25 Jan 2026
CONCERTS

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Upcoming Comedy Events

April Macie from Netflix!

 19 3rd St NW 20 Feb 2026
COMEDY USD 30

Peter Antoniou: Psychic Comedian!

 19 3rd St NW 5 Feb 2026
COMEDY USD 30

Kevin Farley: Yes THAT Farley!

 19 3rd St NW 6 Feb 2026
ENTERTAINMENT USD 30

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Upcoming Food & Drinks Events

Open Mic Renegades

 SoCe Market 29 Mar 2025
PERFORMANCES FREE

Galentine’s Glow: Pajamas & Pottery Breakfast (Winter Haven)

 Art on Fire Studio 14 Feb 2026
GALENTINES-DAY USD 24 TO 46

Central Florida Food Truck Rally (Day 1s of the Rally Special)

 Boys & Girls Clubs of Polk County, George Jenkins Memorial Unit 7 Mar 2026
FOOD-DRINKS USD 13

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Upcoming Festivals Events

Florida's Citrus Festival

 Central Park, Downtown Winter Haven 31 Jan 2026
FESTIVALS

12th Annual 863 Art Fest

 469 W Central Ave, Winter Haven, FL, United States, Florida 33881 18 Apr 2026
FESTIVALS

Joe Pug

 297 5th St NW, Winter Haven, FL, United States, Florida 33881 1 Feb 2026
MUSIC

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Trending Events in Winter Haven

“Mystic Day at Moon Dreamz”

 2750 US-17 N, Winter Haven, FL, United States, Florida 33881 17 Jan 2026
SPEED-DATING

Speed Dating Event Tricks: Guide for Winter Haven Singles

 Winter Haven 4 Jun 2025
SPEED-DATING USD 23 TO 35

Taste of Winter Haven 2026

 Venue 650 22 Jan 2026
NONPROFIT

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

 1006 S Lake Howard Dr, Winter Haven, FL, United States, Florida 33880 16 Jan 2026
SPORTS

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

 Historic Ritz Theatre, Inc 23 Jan 2026
ART USD 19 TO 73

2026 Central Florida Spirit Classic Gymnastics Meet

 Adventhealth Fieldhouse 31 Jan 2026
SPORTS

The Black Market, A Melanin Cultural Festival

 Martin Luther King Jr Park 7 Feb 2026
FESTIVALS FREE

Joe Matarese & Friends!

 19 3rd St NW 15 Jan 2026
COMEDY USD 20

Peter Antoniou: Added Show!

 19 3rd St NW 5 Feb 2026
COMEDY USD 30

Rob Little: MAXIM Comedian of the Year!

 19 3rd St NW 16 Jan 2026
COMEDY USD 25

13th Annual WHPD 5k - 3/14/26

 Winter Haven Public Library 14 Mar 2026

Eric and Mike Podcast: Live Show!

 19 3rd St NW 22 Jan 2026
COMEDY USD 5 TO 10

Phil Johnson from SiriusXM!

 19 3rd St NW 20 Feb 2026
ENTERTAINMENT USD 20

WOOD HOME DECOR WORKSHOP

 5535 Cypress Gardens Blvd Suite 210, Winter Haven, FL 17 Jan 2026
WORKSHOPS

Florida Strong Invite

 Adventhealth Fieldhouse 9 Jan 2026
CONTESTS

More things to do in Winter Haven

Live Music
Comedy
Food & Drinks
Festivals
Speed Dating