Each year approximately 350,000 visitors attend the Winter Park Sidewalk Art Festival, regarded as one of the best arts festivals in the country.
The 66th Winter Park Sidewalk Art Festival takes place this weekend, with the three day event kicking off on Friday, March 21, and running through Sunday, March 23, 2025.
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, with an independent panel of three judges selecting the artists that will exhibit their works.
The festival consistently ranks among the top juried fine-art festivals in the country. National accolades include #3 in Art Fair Source Book’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 Art Fair Calendar's list of Best Art Fairs the festival ranks #6 in America and #1 in the South.
The festival features a wide variety of fine arts and crafts in the following categories: clay, digital art, drawings and pastels, fiber, glass, graphics and printmaking, jewelry, leather, metal, mixed media-2D, mixed media-3D, painting, photography, sculpture, watercolor and wood as well as an Emerging Artists category.
Artists compete for 64 awards totaling $76,500. The Best of Show purchase award was increased in 2019 to $12,000. The festival donates the winning work to the City of Winter Park, and all are on permanent display at the Winter Park Public Library. A $5,000 “Art of Philanthropy” Purchase Award is sponsored by the Edyth Bush Charitable Foundation, while a $2,500 “Distinguished Work of Art” Award is presented through the Charles Hosmer Morse Museum of American Art. New in 2023 is a $2,000 annual “Monte Livermore Celebration of Nature Award”. There are 10 Awards of Excellence of $2,000 each, 20 Awards of Distinction of $1,000 each and 30 Awards of Merit of $500 each.
Kids can create their own artwork at the Children’s Workshop. Easel painting is very popular, and local art centers and museums feature a variety of fun, hands-on art activities for children. Admission is free and participants may take home their artistic creations.
The festival features live music on Friday night. Taking place on the stage in North Central Park when the Winter Park Sidewalk Art Festival presents the 2025 Friday Night Concert. At 5:30 pm they open with the crowd-pleasing band, Brown Bag Brass Band, followed by George Porter Jr. & The Runnin’ Pardners starting at 7:30 pm.
For more details on this year's Winter Park Sidewalk Art Festival, click here.
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