MARCH 21 - 23, 2025


General Information


Application launching in August 2024.

The 66th Winter Park Sidewalk Art Festival will be held March 21 - 23, 2025.

The Winter Park Sidewalk Art Festival is one of the nation’s oldest, largest and most prestigious juried outdoor fine art festivals. It is also one of the nation’s most profitable, positioned at #3 in Art Fair SourceBook’s 2020 rankings by artists sales and #6 in Sunshine Artist’s Top 200 from 2010-2020, a 10-year ranking of the nation’s most profitable art shows.  Also voted #3 All Time Favorite Festival in Sunshine Artist's recent national survey. And listed as #1 Best Festival in the South by Art Fair Calendar.
The Festival debuted in March 1960 as a community project and is still produced today by an all-volunteer board that puts an emphasis on meeting the needs of the artists.  Set in a beautiful, historic downtown setting, the festival draws approximately 250,000 art-loving visitors. Artists from all around the country and beyond apply yearly to this highly competitive and very popular show.  An independent panel of three nationally accomplished judges will select the 212 fine artists and three emerging artists invited to exhibit their works. Emerging artists are encouraged to apply, see full details under the Emerging Artist tab.

Cash Prizes:

  • $76,500 in cash awards ranks among the highest in the country
  • Additional $90,000 plus projected in Patron Bucks
  • Best of Show: $12,000 purchase award

Important Dates:

  • Artist’s Application Deadline: September 25, 2023
  • Jury Notification: November 5, 2023
  • Festival dates: March 15, 16, 17, 2024 

Artists Amenities and Features:

  • Cash prizes and Patron Bucks estimated at $166,500
  • High attendance with 250,000 visitors expected over 3 days
  • Artists’ Hospitality Center with refreshments available all day
  • Booth sitting staffed by volunteers available on call
  • Artist Care Team visiting artists with water and snacks
  • Free artists’ parking near the Park
  • Discount hotel rates
  • Saturday Night Artists’ Dinner & Awards Presentation
  • Art Festival Magazine distributed at event and archived on website
  • Artists’ Gallery on website
  • Security patrol after hours
  • Live music throughout the weekend
  • Set in an affluent art loving community with a robust Patrons Program
  • Extensive media promotions leading up to and during the Festival
  • Artists retain all sales proceeds