The 65th Annual Winter Park Sidewalk Art Festival is one of the nation’s oldest and most prestigious juried fine The Winter Park Sidewalk Art Festival is one of the nation’s oldest, largest and most prestigious outdoor art festivals. The festival debuted in March 1960 as a community project to bring local artists and art lovers together. It’s produced by an all-volunteer board and draws up to 250,000 visitors each year. More than 1000 artists from around the world applied for this year’s event. The festival consistently ranks among the top juried fine-art festivals in the country.  National accolades include #3 in Art Fair SourceBook’s 2020 festival rankings and #6 in Sunshine Artist’s Top 200 from 2010-2020, a 10-year ranking of the nation’s most profitable art shows. In ArtFairCalendar’s list of Best Art Fairs the festival ranks #6 in America and #1 in the South.