Upcoming Winter Haven Events

Check out what's happening all around Winter Haven, FL

Winter Haven Winter Wonderland

Fri, 12 Dec at 06:00 pm Central Park Downtown Winter Haven

I LOVE ROCK N ROLL

Sat, 27 Dec at 08:00 pm Caribbean Bay Bar

Taste of Winter Haven 2026

Thu, 22 Jan at 06:00 pm Venue 650

Open Mic Renegades

Sat, 29 Mar SoCe Market Free

Santa Paws & Friends Holiday Market: Shop, Sip, Snap a Photo!

Sat, 13 Dec at 10:00 am Dog Dayz Cafe Free

A Night of Magic and Sophisticated Buffoonery - Cody’s Comedy Cabaret

Sat, 10 Jan at 07:00 pm Theatre Winter Haven - The GhostLight Lounge USD 17 to 45

Kevin Farley: Yes THAT Farley!

Fri, 06 Feb at 08:00 pm 19 3rd St NW USD 30

December Cookie Exchange

Sat, 20 Dec at 05:00 pm Winter Haven Flordia

Tanyalee Davis from Last Comic Standing!

Fri, 26 Dec at 08:00 pm 19 3rd St NW USD 24

Christmas at RidgePoint

Sun, 14 Dec at 06:00 pm 100 Hatfield Rd, Winter Haven, FL, United States, Florida 33880

Devin Siebold from Bored Teachers!

Sun, 21 Dec at 08:00 pm 19 3rd St NW USD 24

Renard Hirsch from Nateland Presents!

Fri, 09 Jan at 08:00 pm 19 3rd St NW USD 20

Open Mic Renegades

Sat, 20 Dec at 06:30 pm SoCe Market

FPW Wrestling Live at Tanners Lakeside

Fri, 12 Dec at 07:00 pm 1006 S Lake Howard Dr, Winter Haven, FL, United States, Florida 33880

Christmas Caroling

Fri, 19 Dec at 06:00 pm 301 6th St NE Winter Haven, FL 33881

KARAOKE NIGHT AT KULTURE ON 1ST

Thu, 25 Sep KULTURE ON 1ST Free

Winter Haven SantaCon 2025

Sat, 20 Dec at 06:00 pm Downtown Winter Haven Historic District

Live Music at Bowen Yard

Sat, 13 Dec at 05:30 pm 308 Fourth St SW, Winter Haven, FL, United States, Florida 33880

Forrest Shaw from Netflix is a Joke!

Sat, 20 Dec at 08:00 pm 19 3rd St NW USD 24

An Evening With Burning Leafs

Sat, 20 Dec at 05:00 pm 301 3rd St NW USD 31 to 48

Magic - Avatar: The Last Airbender - Draft League

Sat, 13 Dec at 05:00 pm 6260 Cypress Gardens Blvd., Winter Haven, FL, United States, Florida 33884

Live Music at Bowen Yard

Fri, 12 Dec at 05:30 pm 308 Fourth St SW, Winter Haven, FL, United States, Florida 33880

Joey Kirkland SOLO at Twisted Prop

Sat, 13 Dec at 06:00 pm The Twisted Prop Bar & Grille

2025 CARS Racin' For A Dream Charity Race

Sat, 13 Dec at 05:00 pm 5640 State Road 542 W, Winter Haven, FL, United States, Florida 33880

Empower & Elevate 2026 | Vision Board + Holistic Goal Setting Experience

Sat, 10 Jan at 11:00 am AR Workshop Winter Haven USD 53

Josh Blevins Live at Tanners Lakeside

Sat, 13 Dec at 07:00 pm 1006 S Lake Howard Dr, Winter Haven, FL, United States, Florida 33880

The Got Ur 6 Band Rocks The Bay Toy 4 Our Town

Sat, 13 Dec at 08:00 pm Carribbean Bay Bar

Ric Diez from K*ll Tony!

Fri, 12 Dec 19 3rd St NW USD 24

Plaid Tidings - SecondStage

Thu, 11 Dec at 07:00 pm 210 Cypress Gardens Blvd SW, Winter Haven, FL, United States, Florida 33880

It's A Twizted Party!

Sun, 04 Jan at 03:00 pm Caribbean Bay

Heartfulness

Sun, 21 Dec at 11:00 am 1511 6th St SE, Winter Haven, FL, United States, Florida 33880

Cordero Music Presents Youth Music Night

Fri, 23 Jan at 05:30 pm Bowen Yard Free

Peter Antoniou: Psychic Comedian!

Thu, 05 Feb at 08:00 pm 19 3rd St NW USD 30

Live and Loud at the Ritz

Fri, 02 Jan at 06:00 pm The Ritz

Derek Luna from WSOC!

Fri, 02 Jan at 08:00 pm 19 3rd St NW USD 20

Dormancy Workshop: How to Care for Sleeping Plants

Sat, 20 Dec at 11:00 am 6405 Thornhill Rd, Winter Haven, FL 33880-5037, United States

April Macie from Netflix!

Fri, 20 Feb at 08:00 pm 19 3rd St NW USD 30

Grinchmas at Gourmet Goodies 2025

Fri, 12 Dec at 04:00 pm 68 4th St NW, Winter Haven, FL, United States, Florida 33881

Christmas Festival at The Ranch

Thu, 25 Dec at 11:00 am 5615 Recker Highway Winter Haven

The Roast of Christmas!

Thu, 18 Dec at 08:00 pm 19 3rd St NW USD 19

Learning with Littles playgroup -- Christmas Senses

Fri, 12 Dec at 10:30 am 1449 34th Street NW, Winter Haven, FL, United States, Florida 33881

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

Sat, 14 Feb at 09:30 am Art on Fire Studio USD 24 to 46

Mr. Ed's Annual Christmas Jam with Jimmy Elkins and Friends.

Sat, 27 Dec at 07:00 pm La's Midway Saloon

Rob Little: MAXIM Comedian of the Year!

Fri, 16 Jan at 08:00 pm 19 3rd St NW USD 25

Star Wars Unlimited - Premiere Constructed

Sat, 13 Dec at 01:30 pm 6260 Cypress Gardens Blvd., Winter Haven, FL, United States, Florida 33884

Smokepoint Returns to Tanners Lakeside

Sat, 27 Dec at 07:00 pm Tanners Lakeside

Thursday Night Karaoke w/ChingChing

Thu, 11 Dec at 06:00 pm Caribbean Bay

Rob Smiles & Friends!

Thu, 08 Jan at 08:00 pm 19 3rd St NW USD 8 to 15

“Rodney’s Mediumship Circle”

Thu, 18 Dec at 06:00 pm 2750 US-17 N, Winter Haven, FL, United States, Florida 33881

Christmas at the Barn

Sat, 13 Dec at 05:00 pm 3805 High Street, Winter Haven, FL, United States, Florida 33881

Magic - Lorwyn Eclipsed Prerelease (Friday)

Fri, 16 Jan at 06:00 pm 6260 Cypress Gardens Blvd., Winter Haven, FL, United States, Florida 33884

Magic - Avatar: The Last Airbender Commander BINGO Party

Thu, 11 Dec at 06:00 pm 6260 Cypress Gardens Blvd., Winter Haven, FL, United States, Florida 33884

Florida Pro Wrestling

Fri, 12 Dec at 08:00 pm Tanners Lakeside

Cordero Music Presents Youth Music Night

Sat, 28 Feb at 05:30 pm Bowen Yard Free

Patrick Garrity: The Never Ending Tour!

Fri, 23 Jan at 08:00 pm 19 3rd St NW USD 20

Winter Haven Farmers Market

Sat, 13 Dec at 09:00 am 250 Magnolia Ave, Winter Haven, FL, United States, Florida 33880

99 in the Shade at Somewhere Sports Bar and Grill!

Fri, 12 Dec at 07:00 pm Somewhere Sports Bar and Grill

Bingo Night At Bowen Yard

Wed, 17 Dec at 06:00 pm 308 Fourth St SW, Winter Haven, FL, United States, Florida 33880

Sweetheart Showcase

Sat, 14 Feb at 06:00 pm El Shaddai Community Church USD 88 to 214

Magic - Pauper Cube Draft 2

Sat, 03 Jan at 01:30 pm 6260 Cypress Gardens Blvd., Winter Haven, FL, United States, Florida 33884

Daniel Burns Band Last Show of 2025 @ The Twisted Prop Bar & Grille

Fri, 19 Dec at 06:00 pm The Twisted Prop Bar & Grille

April Red ROCKS the TIKI at Caribbean Bay Bar in Winter Haven!

Sat, 20 Dec at 02:00 pm Carribbean Bay Bar

Hunter McNeer Live at Old Man Franks

Sat, 13 Dec at 01:00 pm 1005 S Lake Howard Dr, Winter Haven, FL, United States, Florida 33880

An Evening with Burning Leafs

Sat, 20 Dec at 05:00 pm Winterhaven,Fl.

“Yule at Moon Dreamz”

Fri, 19 Dec at 07:45 pm 2750 US-17 N, Winter Haven, FL, United States, Florida 33881

Pottery Date Night

Fri, 12 Dec at 06:30 pm Ridge Art Association

GOLD RUSH SALES EVENT!

Fri, 12 Dec at 09:00 am 621 Cypress Gardens Blvd, Winter Haven, FL

Yu-Gi-Oh - Locals - Advanced

Sun, 14 Dec at 02:00 pm 6260 Cypress Gardens Blvd., Winter Haven, FL, United States, Florida 33884

B.Haven Live at Somewhere Sports Bar

Sat, 20 Dec at 07:00 pm Somewhere Sports Bar and Grill

Magic - Pauper Cube Draft 3

Sat, 10 Jan at 01:30 pm 6260 Cypress Gardens Blvd., Winter Haven, FL, United States, Florida 33884

Jingle Mingle Mixer - Sarner's 1st Soiree!

Sat, 20 Dec at 05:00 pm Sarner Pass Way

Got Ur 6 Band “Toys 4 Our Town” Toy Drive

Fri, 12 Dec at 07:00 pm Winter Haven Moose Lodge 1023 & Chapter 1152

Magic - Lorwyn Eclipsed Store Championship (Standard)

Fri, 06 Feb at 06:00 pm 6260 Cypress Gardens Blvd., Winter Haven, FL, United States, Florida 33884

Joe Matarese & Friends!

Thu, 15 Jan at 08:00 pm 19 3rd St NW USD 20

Deck the Yard

Sat, 13 Dec at 02:00 pm 308 Fourth St SW, Winter Haven, FL, United States, Florida 33880

Free Pup Swag Bag at Pet Fest 2025!

Sat, 13 Dec at 10:00 am 7115 De Castro Rd Free

Lorcana - Magical Monday - Core Constructed

Mon, 15 Dec at 06:00 pm 6260 Cypress Gardens Blvd., Winter Haven, FL, United States, Florida 33884

Mental Health Art Workshop | Spread Kindness: Painting Watercolor Cards

Sat, 13 Dec at 11:00 am 5624 Cypress Gardens Blvd Free

World of Figure 8 - 100 laps

Sat, 21 Feb at 06:00 pm 5640 State Road 542 W, Winter Haven, FL, United States, Florida 33880

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

Fri, 23 Jan at 07:00 pm Historic Ritz Theatre, Inc USD 19 to 73

The Encounter Meeting

Sat, 03 Jan at 09:00 am St Joseph Catholic Church, Winter Haven, Florida (Ministry Building)

Conspiracy Theory Rocks New Years at Kimbers Bar and Grill

Wed, 31 Dec at 08:00 pm Kimber's Bar and Grill

Work Sucks: A Comedy Showcase!

Thu, 11 Dec at 08:00 pm 19 3rd St NW USD 10 to 19

First Friday Winter Haven

Fri, 02 Jan at 05:00 pm Downtown Winter Haven Historic District

Free Ski Show!!!! Please share. Follow us on Facebook and Instagram

Sat, 20 Dec at 03:15 pm 275 South Lake Silver Dr, Winter Haven, FL, United States, Florida 33881

Middle School Sneaker Ball

Fri, 12 Dec at 06:00 pm Grace Lutheran School

Winter Haven Saturday Markets

Sat, 13 Dec at 09:00 am 469 W Central Ave, Winter Haven, FL, United States, Florida 33881

“Tarot Practice w/ Cheryl”

Sun, 14 Dec at 06:00 pm 2750 US-17 N, Winter Haven, FL, United States, Florida 33881

Joe Pug

Sun, 01 Feb at 06:00 pm 297 5th St NW, Winter Haven, FL, United States, Florida 33881

Night of Worship with Julie Elias & Al Denson

Sun, 14 Dec at 06:00 pm 2101 Overlook Dr, Winter Haven, FL

The Got Ur 6 Band Rocks Old Man Franks (Toys 4 Our Town) Toy Drive

Fri, 19 Dec at 07:00 pm Old Man Frank's

Candlelight Christmas Service

Sun, 14 Dec at 06:00 pm 560 3rd St SW, Winter Haven, FL

Spagehetti Dinner

Fri, 12 Dec at 05:00 pm 180 Avenue A SE, Winter Haven, FL 33880-6301, United States

Magic - Pauper Cube Draft

Sat, 27 Dec at 05:30 pm 6260 Cypress Gardens Blvd., Winter Haven, FL, United States, Florida 33884

Nick Giasullo from Snap Battles!

Fri, 23 Jan at 08:00 pm 19 3rd St NW USD 20

People's Church Merry and Bright Ladies Night

Sat, 20 Dec at 04:30 pm 3800 Recker Hwy, Winter Haven, FL, United States, Florida 33880

Dessert Fundraising

Fri, 12 Dec at 05:00 pm 180 Avenue A SE, Winter Haven, FL 33880-6301, United States

A Very Merry Small Team Christmas! 🎄✨

Fri, 12 Dec at 04:00 pm 786 Avenue C SW, Winter Haven, FL 33880-2809, United States

Daniel Pepin live at The Social Cocktail Lounge

Sat, 20 Dec at 09:00 pm The Social Cocktail Lounge

“MRG” (Metaphysical Research Meeting)

Thu, 11 Dec at 08:00 pm 2750 US-17 N, Winter Haven, FL, United States, Florida 33881

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