Festivals in Winter Park

• Fri, 20 Mar, 2026 - 09:00 AM

  The 67th Winter Park Sidewalk Art Festival

  Park Avenue, Winter Park

  13+ Interested
• Wed, 01 Apr, 2026 - 06:30 PM

  Taste of Winter Park

  Winter Park Farmers' Market Venue

  14+ Interested

  |

  USD 55
• Fri, 20 Mar, 2026 - 09:30 AM

  Winter Park Sidewalk Art Festival Celebration

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

  3750+ Interested
• Fri, 12 Mar, 2027 - 09:00 AM

  Winter Park Art Festival

  Park Avenue, Winter Park
• Fri, 20 Mar, 2026 - 06:00 PM

  Winter Park Arts Festival

  Winter Park Florida
• Thu, 26 Mar, 2026 - 07:00 PM

  Free: Jazz Festival—Live with The Yo Cats

  Winter Park Events Center

  Free
• Sat, 21 Mar, 2026 - 10:00 AM

  Live Painting at George's Cafe in Winter Park

  George's Cafe in Winter Park

  19+ 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

  24+ Interested
• Sat, 28 Mar, 2026 - 12:00 PM

  Romancing the Books Festival 2026 | Keynote: Meryl Wilsner

  Winter Park Library

  Free
• Wed, 20 May, 2026 - 07:00 PM

  Arankai at Conduit

  Conduit