Winter Haven Holiday Events

Holiday events Happening Next in Winter Haven, FL

Christmas Boat Parade

 Lake Howard Dr, Winter Haven, FL, United States 6 Dec 2025
CHRISTMAS-PARADES

Plaid Tidings - SecondStage

 210 Cypress Gardens Blvd SW, Winter Haven, FL, United States, Florida 33880 4 Dec 2025
CHRISTMAS

Fantaseay Dezires Presents Naughty or Nice; A Holiday Social

 Venue 650 6 Dec 2025
HOLIDAY USD 25 TO 59

Havendale Christmas Parade

 Havendale Blvd NW, Winter Haven, FL 33881, United States 5 Dec 2025
CHRISTMAS-PARADES

Bad Santa & The Angry Elves

 Jessie's Lounge 6 Dec 2025
HOLIDAY USD 19

Santa’s house by the Bigda’s opening night

Winter Haven Flordia 6 Dec 2025
NONPROFIT

Tree Lighting Ceremony

 Central Park Downtown Winter Haven 4 Dec 2025
CHRISTMAS-LIGHTS

The Roast of Christmas!

 19 3rd St NW 18 Dec 2025
CHRISTMAS USD 19

Mental Health Art Workshop | Spread Kindness: Painting Watercolor Cards

 5624 Cypress Gardens Blvd 13 Dec 2025
ART FREE

Winter Haven Winter Wonderland

 Central Park Downtown Winter Haven 12 Dec 2025
CHRISTMAS

99 in the Shade at Somewhere Sports Bar and Grill!

Somewhere Sports Bar and Grill 12 Dec 2025
SPORTS

Holidays on Central

 Central Park in Downtown Winter Haven 6 Dec 2025
HOLIDAY

The Chain O’ Lakes Big Band at American Legion Post 8

 300 Ave M NW, Winter Haven, FL 33881 23 Nov 2025
MUSIC

Small Business Saturday

 369 3rd street nw, Winter Haven, FL 29 Nov 2025
HOLIDAY

Camellia Groves First Annual Limoncello Festival

 839 State Rd 540 W 7 Dec 2025
FESTIVALS USD 23

An Evening With Burning Leafs

 301 3rd St NW 20 Dec 2025
MUSIC USD 31 TO 48

WRC's Annual Toy Drive

 165 Avenue A NW, Winter Haven, FL, United States, Florida 33881 5 Dec 2025
NONPROFIT

Humane Society's Santa Paws 2025

 Jensen's Corner Bar 9 Dec 2025
MUSIC

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

 Dog Dayz Cafe 13 Dec 2025
CHRISTMAS-MARKETS-AND-FAIRS FREE

Small Business Saturday at Spa Haven

700 Overlook Drive, Winter Haven, FL, United States, Florida 33884 29 Nov 2025
HOLIDAY

December Cookie Exchange

Winter Haven Flordia 20 Dec 2025
HOLIDAY

Christmas Cookie Decorating Party

 SPA HAVEN 4 Dec 2025
PARTIES

6 O'Clock Social @ Ave Bar

 Ave Bar by Arabellas 2 Dec 2025
HOLIDAY

Turkey Trot & Paddle

 Lake Summit Park West 27 Nov 2025
TURKEY-TROT

Bloomsgiving: U-Pick Flowers!

 6405 Thornhill Rd, Winter Haven, FL 33880-5037, United States 25 Nov 2025
THANKSGIVING

Save The Date 📅 Annual Holiday Party 🎄🎅🏼🎁

 Spring Lake Rehabilitation Center 17 Dec 2025
HOLIDAY

Festival of Trees- Mistletoe Mixer Preview Party

The Packing House at Grove Roots 21 Nov 2025
FESTIVALS

Christmas/Holiday Banner Painting Party

 Vienna Square 5 Dec 2025
PARTIES