Winter Haven is set for a festive and activity-packed this weekend, offering a full lineup of community events for families, holiday lovers, and residents looking to celebrate the season in true Winter Haven style.
One of the weekend’s biggest highlights is the Cypress Gardens Water Ski Show, returning to Lake Silver with its signature blend of high-energy stunts and holiday-themed performances. The pre-show begins at 3:15 PM on December 20, followed by the main show at 4:00 PM. This long-standing local tradition is free to attend and draws spectators from across Central Florida every year.
Saturday starts bright and early at Central Park in downtown Winter Haven, where the Winter Haven Saturday Market will be open from 9 AM. Guests can shop local vendors, browse handcrafted goods, and enjoy seasonal treats—perfect for those finishing up their holiday shopping.
Families can head over to the Winter Haven Public Library after for a festive twist on a classic event: the Holiday “Drive-In” from 2:00 to 4:30 PM. Kids can decorate their own cardboard “cars” and then settle in to enjoy a fun holiday movie inside the library.
Rounding out the day is the lively and much-anticipated 2025 Winter Haven SantaCon, where participants dress as Santa and spread cheer throughout the community. The event brings a playful, spirited atmosphere to the city as groups of Santas visit local businesses, take photos, and enjoy the holiday season together.
With family fun, festive traditions, local shopping, and one-of-a-kind entertainment, Winter Haven is ready to celebrate this weekend in a big way.
