Winter Haven is gearing up for a full weekend of activities, offering everything from live entertainment to outdoor adventures and holiday fun. Here’s a roundup of what’s happening around town.
Friday, November 14
Main Street Winter Haven will host a delightful Wine, Chocolate, and Cheese night from 5:30-8:30 p.m.
Saturday, November 15
The day is packed with family-friendly and outdoor events, including the Cypress Gardens Water Ski Team Show starting at 3:30 p.m. and the Winter Haven Farmers Market,
Downtown Winter Haven will also host the Haven Holiday Market from 10 a.m.–4 p.m.
Winter Haven Public Library is hosting Swap til you Drop, a community plant swap, from 2-5 p.m.
Families can enjoy the Break Your Fall – Family Fall Festival from 4–7 p.m. at Garden Grove Church, featuring inflatables, food, games, and more.
For outdoor enthusiasts, the Kayak Ecotour & Chain Reaction Cleanup runs from 9 a.m.–12 p.m. at Lake Cannon Park—offering a guided kayak tour while helping clean local waterways.
Winter Haven has something for everyone—get out, explore, and enjoy the weekend!


