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Submit four images (three artwork completed in 2020 or after, one booth shot) for jurying into this prestigious outdoor fine art festival.
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Get matched →The 68th Annual Winter Park Sidewalk Art Festival is one of the nation's oldest and most prestigious juried fine art shows. Ranked #8 in the nation in 2025 by Art Fair SourceBook, it features 218 artists and 3 emerging artists over a three-day event in historic downtown Winter Park, Florida. Expected attendance exceeds 250,000. A portion of proceeds benefits scholarships through Rollins College and the University of Central Florida.
Must be at least 18 years of age. Artwork must be substantially the same as shown in submitted images; non-compliance may result in expulsion from the show. Previous WPSAF award-winning artwork is not eligible for awards. The festival is family-oriented; artwork featuring nudity must portray the human body in a respectful and non-exploitative manner.
Application fee is $45.00 (non-refundable). Exhibitor/Booth Fee due by December 7, 2026. Refund requests accepted through December 31, 2026, subject to a $35.00 administrative fee.
Every listing links to the organizer's official page. Always confirm deadlines, fees, and entry rules there before you apply.
Three independent judges selected from across the country will review digital images in October to select festival and waitlist artists. The same judges will review exhibited work in March to determine award eligibility based on overall quality. Artists select one piece for Saturday's awards processing that best represents their entire body of work.