
John is honored to have been invited to judge this exceptional art festival and we hope those in the area will get a chance to view the exhibit, plus experience the many other activities offered, like Music and Food, the Children’s Workshop and the Leon Theodore Schools Exhibit.... click here to learn more.

When: May 14, 15, 16, 2021
Hours: 9 a.m. – 6 p.m., Friday and Saturday; 9 a.m. – 5 p.m., Sunday
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. An independent panel of three judges select 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.
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.
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.