Clearwater's Winter Wonderland Festival

Nov 29, 2025 – Dec 23, 2025

See All Dates & Times
Outdoor nightly Winter Wonderland holiday festival featuring a stage with people watching a show.

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

  • 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

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