Clearwater's Winter Wonderland Festival
Nov 29, 2025 – Dec 23, 2025
See All Dates & Times
The 32nd Annual Winter Wonderland features all of the fun activities to get you into the holiday spirit! Including a fun entertainment stage, Santa photo ops, cookie decorating with Mrs. Claus, a cozy hot chocolate stand, and cheerful rides on the Holiday Express Train. You can also enjoy seasonal favorites like pony rides, bounce houses, and plenty more—all set in a beautifully lit village that really captures the holiday spirit.
Admission is free, and visitors are encouraged to bring a non-perishable food item or unwrapped toy to benefit local charities, including the Pinellas Sheriff’s Police Athletic League of Lealman. With its warm atmosphere, continuous entertainment, and a strong sense of community, Winter Wonderland has become a holiday tradition for families across Pinellas County and beyond!
Event Category
- Annual Festivals & Events
- Arts & Crafts
- Festivals
- Food + Drink
- Kids
- Music & Concerts
Guest Information
- Family-Friendly
- Free Admission
- Outdoor Event
Event Dates for the month of
- Saturday, November 29, 2025 - 6:00 pm
- Sunday, November 30, 2025 - 6:00 pm
- Monday, December 1, 2025 - 6:00 pm
- Tuesday, December 2, 2025 - 6:00 pm
- Wednesday, December 3, 2025 - 6:00 pm
- Thursday, December 4, 2025 - 6:00 pm
- Friday, December 5, 2025 - 6:00 pm
- Saturday, December 6, 2025 - 6:00 pm
- Sunday, December 7, 2025 - 6:00 pm
- Monday, December 8, 2025 - 6:00 pm
- Tuesday, December 9, 2025 - 6:00 pm
- Wednesday, December 10, 2025 - 6:00 pm
- Thursday, December 11, 2025 - 6:00 pm
- Friday, December 12, 2025 - 6:00 pm
- Saturday, December 13, 2025 - 6:00 pm
- Sunday, December 14, 2025 - 6:00 pm
- Monday, December 15, 2025 - 6:00 pm
- Tuesday, December 16, 2025 - 6:00 pm
- Wednesday, December 17, 2025 - 6:00 pm
- Thursday, December 18, 2025 - 6:00 pm
- Friday, December 19, 2025 - 6:00 pm
- Saturday, December 20, 2025 - 6:00 pm
- Sunday, December 21, 2025 - 6:00 pm
- Monday, December 22, 2025 - 6:00 pm
- Tuesday, December 23, 2025 - 6:00 pm