Winter Haven is kicking off the holiday season with a festive lineup of celebrations, parades, and family-friendly activities. From dazzling lights on the lakes to downtown holiday markets, here’s your guide to everything happening December 4–6, 2025.
City of Winter Haven Tree Lighting — December 4
Winter Haven officially welcomes the holiday season on Thursday with its annual Tree Lighting at Central Park in downtown. From 6:00 PM to 8:00 PM, guests can enjoy live holiday music, participate in a community countdown, and watch as the city’s official Christmas tree comes to life. The first 100 children will receive free cookies and hot chocolate, creating the perfect cozy start to the festive weekend.
Havendale Christmas Parade — December 5
The holiday magic continues Friday evening with the beloved Havendale Christmas Parade. Running from 7:00 PM to 9:00 PM, the parade travels along Havendale Boulevard, starting in Winter Haven and heading toward Auburndale. Expect sparkling floats, cheerful music, and plenty of community spirit as families line the roadway to enjoy this cherished tradition.
Holidays on Central — December 6
Downtown Winter Haven transforms into a holiday village on Saturday for the all-day Holidays on Central celebration. Centered around Central Park, this event features more than 100 local vendors, live entertainment, delicious seasonal treats, food trucks, and photo opportunities with Santa. It’s an ideal place to find unique gifts, enjoy festive activities, and soak in the spirit of the season.
Winter Haven Chain of Lakes Christmas Boat Parade — December 6
Saturday night brings one of Winter Haven’s most iconic holiday traditions: the Chain of Lakes Christmas Boat Parade. Beginning at 6:30 PM, boats decked out in dazzling lights cruise from Lake May through Lake Howard before ending at Lake Shipp. Spectators gather along the shorelines to watch the colorful procession reflect off the water — a breathtaking sight that captures the beauty of the holidays in Winter Haven.
