Named America’s Best Juried Fine Art Fair (Art Fair Calendar, 2013 & 2014), The Winter Park Sidewalk Art Festival is one of the nation’s oldest, largest and most prestigious outdoor art festivals. It is also ranked the #1 Best Fine Art and Design Show in the southeast and #5 in the Nation by Sunshine Artist Magazine, 2014. The Festival debuted in March 1960 as a community project to bring local artists and art lovers together. The Festival is produced by an all-volunteer board and draws more than 350,000 visitors each year. This year, more than 1,100 artists from around the world applied for entry. An independent panel of three judges selected the 225 artists exhibiting their works. The Festival is also recognized as “Central Florida’s Best Festival,” Orlando Magazine, 2013 & 2014; and “Best Winter Park Event/Festival,” The Winter Park Chamber of Commerce and Winter Park / Maitland Observer, 2013 & 2014.
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 as well as our Emerging Artists.
Artists complete for 63 awards totaling $72,500. The Best of Show winner is purchased for $10,000 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.
Girls and boys can create their own artwork at the Children’s Workshop Village. 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 Village 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.