- March 21, 2025
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The Winter Park Sidewalk Art Festival takes place this weekend.
The festival takes place in Central Park and along Park Avenue in Winter Park. Festival hours are 9 a.m. to 6 p.m., Friday, March 21, and Saturday March 22; and 9 a.m. to 5 p.m., Sunday, March 23.
The hours for the Leon Theodore Schools Exhibit are 9 a.m. to 5 p.m, Friday, March 21, and Saturday March 22; and 9 a.m to 3:30 p.m., Sunday, March 23.
The 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 1,000 artists from around the world applied for this year’s event. An independent panel of three judges select the artists that will exhibit their works.
The Leon Theodore Schools Exhibit will feature artwork from students from many West Orange and Southwest Orange schools, including Foundation Academy, Gotha Middle School, Horizon West Middle School, Ocoee Middle School, SunRidge Middle School, Water Spring Middle School, Windy Ridge K-8, Dr. Phillips High School, Horizon High School, Olympia High School, The First Academy, West Orange High School and Windermere High School.
The festival consistently ranks among the top juried fine-art festivals in the country.