Winter Haven Holiday Events

Winter Haven Winter Wonderland

Central Park Downtown Winter Haven 12 Dec 2025

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

Dog Dayz Cafe 13 Dec 2025

December Cookie Exchange

Winter Haven Flordia 20 Dec 2025

Winter Haven SantaCon 2025

Downtown Winter Haven Historic District 20 Dec 2025

An Evening With Burning Leafs

301 3rd St NW 20 Dec 2025

The Roast of Christmas!

19 3rd St NW 18 Dec 2025

99 in the Shade at Somewhere Sports Bar and Grill!

Somewhere Sports Bar and Grill 12 Dec 2025

Mental Health Art Workshop | Spread Kindness: Painting Watercolor Cards

5624 Cypress Gardens Blvd 13 Dec 2025

A Very Merry Small Team Christmas! 🎄✨

786 Avenue C SW, Winter Haven, FL 33880-2809, United States 12 Dec 2025

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

Old Man Frank's 19 Dec 2025

Santa & The Grinch Photo Experience 💚

1047 Corso Drive Winter Haven, Florida 33884 21 Dec 2025

FREE Toys for Kids! Posada Navideña at Tu Plaza Market🎄

200 Post Ave SW, Winter Haven, FL 18 Dec 2025

December Social at Grove Roots!

Grove Roots Brewing Co. 16 Dec 2025