Festivals in Winter Park

• Wed, 01 Apr, 2026 - 06:30 PM

  Taste of Winter Park

  Winter Park Farmers' Market Venue

  USD 55
• Sat, 14 Mar, 2026 - 05:00 PM

  1st Annual Holler Ford Racing Showcase

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

  93+ Interested
• Sat, 14 Mar, 2026 - 08:00 AM

  Smile Mile - Kids Run

  Blue Jacket Park

  140+ Interested
• Fri, 20 Mar, 2026 - 09:30 AM

  Winter Park Sidewalk Art Festival Celebration

  445 N Park Ave, Winter Park, FL, United States, Florida 32789

  324+ Interested
• Thu, 26 Mar, 2026 - 07:00 PM

  Free: Jazz Festival—Live with The Yo Cats

  Winter Park Events Center

  Free
• 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

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

  The 67th Winter Park Sidewalk Art Festival

  Park Avenue, Winter Park
• Sat, 28 Feb, 2026 - 10:00 AM

  26th Annual Family Fair & Auction

  International Community School

  48+ Interested
• Wed, 20 May, 2026 - 07:00 PM

  Arankai at Conduit

  Conduit