Winter Park Sidewalk Art Festival

Park Ave Magazine | Winter Park Florida

Winter Park Sidewalk Art Festival

150 W Morse Blvd

Winter Park, FL 32789

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 is produced by an all-volunteer board and draws more than 350,000 visitors each year. Over 1,100 artists from around the world apply for the Festival each year. Festival. An independent panel of three judges selects the 225 artists who will exhibit their works. The Festival consistently ranks as one of the top juried fine art festivals in the country with high rankings in Art Fair Calendar’s “2019 Best Art Fairs”, Art Fair Source Book’s rankings, and Sunshine Artist Magazine’s “Top 100” lists. The 2021 Artists Application is by invitation only this year and is being extended to the final 2020 accepted artists.

About The Festival


The Festival features a wide variety of fine arts and crafts in the following categories: clay, digital art, drawings & pastels, fiber-glass, graphics & printmaking, jewelry, leather, metal, mixed media 2D, mixed media 3D, painting, photography, sculpture, watercolor, and wood, along with a special category for  Emerging Artists.


Artists complete for 63 awards totaling $74,500. The Best of Show winner is purchased for $12,000 by The Winter Park Sidewalk Art Festival Board and donated to the City of Winter Park. Previous Best of Show winners 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. A $2,500 “Distinguished Work of Art” Award is presented through The Charles Hosmer Morse Museum of American Art. 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. In addition to these awards, the Patrons Program generates another $80,000 in Art Bucks that are dedicated to the purchase of artwork.


Girls and boys 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 Children’s Workshop hours are 10 a.m. – 4 p.m. on Friday, Saturday, and Sunday. Easel painting is from 10 a.m. – 3 p.m. on Saturday and Sunday.

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