The 67th Winter Park Sidewalk Art Festival 2026

The 67th Annual Winter Park Sidewalk Art Festival is one of the nation's oldest and most prestigious juried fine art shows. It consistently ranks among the most highly regarded outdoor art shows in the nation, with cash awards totaling $76,500 and dedicated Patron purchase funds expected to be over $100,000. In 2021, the festival was named #4 Best Show of All Times in Sunshine Artist's national poll of All Time Favorites. In 2024 the festival ranked #8 in the USA Today Readers' Choice, 10 Best Art Festivals contest.

The show is located in historic downtown Winter Park, Florida, nestled throughout Central Park and stretching along Park Avenue. The event takes place on March 20-22, 2026, in the heart of this charming city. Attendance at the Festival is expected to reach over 250,000 people who will view the artwork of 215 artists and 3 emerging artists. One of Central Florida's largest annual outdoor events, the Festival also features a wide variety of entertainment on the stage in Central Park, food and beverage to please the whole family, a popular exhibit of student art from Central Florida schools, and many interactive arts for the kids.

Applications are due by September 23, 2025, with a $45 non-refundable application fee. Artists must submit four images: three of artwork with no signatures or initials and one booth image of current artwork created after 2020 with no identifying markers. Artists may apply in up to three different categories but only two entries may be accepted. Must be at least eighteen years of age to apply. Awards include Best of Show ($12,000), Edyth Bush Charitable Foundation Art of Philanthropy ($5,000), ten Awards of Excellence ($2,000 each), twenty Awards of Distinction ($1,000 each), and thirty Awards of Merit ($500 each). A portion of the Festival's proceeds is donated to The Winter Park Sidewalk Art Festival Foundation to fund scholarships.