The 68th 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 2025 the festival ranked #8 in the nation in Art Fair SourceBook's top fine art festivals and was named #4 Best Show of All Times in Sunshine Artist’s national poll of All Time Favorites in 2021. 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 19 – March 21, 2027, 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 218 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.
A portion of the Festival’s proceeds is donated to The Winter Park Sidewalk Art Festival Foundation to fund scholarships through the Jean Alice Oliphant Scholarship at Rollins College and The Winter Park Sidewalk Art Festival Scholarship at the University of Central Florida.
Average number of applications submitted each year
1000
Average number of artists selected from the jury to participate in the event
215
Average number of exempt from jury artists who are invited to participate in the event
34
FEES
Exhibit Booth Fee: $575

Application Fee: $45