Festivals in Winter Park

• Sat, 14 Mar, 2026 - 08:00 AM

  Smile Mile - Kids Run

  Blue Jacket Park

  118+ Interested
• Sat, 14 Mar, 2026 - 05:00 PM

  1st Annual Holler Ford Racing Showcase

  1875 South Orlando Avenue, Maitland, FL, United States, Florida 32751

  35+ Interested
• Sat, 02 May, 2026 - 04:30 PM

  Derby on Park (Kentucky Derby Party)

  Winter Park Events Center

  349+ Interested
• Fri, 30 Jan, 2026 - 05:00 PM

  Florida Dungeon Fest II at Conduit

  Conduit

  370+ Interested
• Sat, 19 Sep, 2026 - 09:00 AM

  Peace Day in the Park

  Central Park Main Stage

  Free
• Fri, 17 Apr, 2026 - 06:00 PM

  25th Annual Orange Blossom Jubilee "Under the Big Top"

  Winter Park Events Center

  17+ Interested
• Sat, 21 Feb, 2026 - 11:00 AM

  ARMAGEDDON 3 ARMWRESTLING TOURNAMENT

  Ain't Missbehavin

  243+ Interested
• Fri, 20 Mar, 2026 - 09:00 AM

  The 67th Winter Park Sidewalk Art Festival

  Park Avenue, Winter Park
• Thu, 05 Feb, 2026 - 03:30 PM

  Trinity Prep's 11th Annual Author Fest

  Trinity Preparatory School

  Free
• Wed, 04 Feb, 2026 - 12:00 AM

  Dinosaur Pile-Up

  Conduit
• Thu, 12 Feb, 2026 - 07:00 PM

  Wheel, Sound and Shape, and More in Orlando

  Conduit

  USD 23