Winter Park Sidewalk Art Festival 2020

Park Ave Magazine | Winter Park Florida

Winter Park Sidewalk Art Festival 2020

Visit the Winter Park Sidewalk Art Festival 2020. Central FL has celebrated The Winter Park Sidewalk Art Festival for 59 years! Voted “America’s Best Juried Fine Art Fair” & “#1 Fine Art Show in the SE”.


The Winter Park Sidewalk Art Festival is one of the nation’s oldest, largest and most prestigious outdoor fine arts & fine crafts festivals. Organized and run by a dedicated group of volunteers, the juried show is nationally recognized and is named the #5 Fine Art Show in the country by Sunshine Artist Magazine in their September 2014 issue. The festival features all original artwork that has been designed and executed by the exhibiting artists during the past two years. The show is conveniently located in Central Park, a beautifully landscaped area whose surrounding streets are closed during the festival to allow for foot traffic only. Many artist booths line Winter Park’s Park Avenue, the heart of a charming downtown with brick-lined streets, unique boutique shops, and multiple outdoor cafes and bistros. Attendance usually exceeds 350,000 people for the three-day event. There are no more than 225 artists selected for participation each year.


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. The Winter Park Sidewalk Art Festival Board has purchased it. Then it is donated to the City of Winter Park. Previous Best of Show winners are on permanent display at the Winter Park Public Library. The Edyth Bush Charitable Foundation sponsors $5,000 “Art of Philanthropy” Purchase Award. 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. 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.


The place to discover the talented artists of the next generation. The Leon Theodore Schools Exhibit is where artwork by thousands of Orange County students is on display. The creativity and level of expertise displayed by these young artists will delight and amaze you. Be sure to check out this wonderful exhibit.


Should you use your bicycle as your means of transportation to the Festival, the City of Winter Park’s Transportation Advisory Board has provided a free bike corral located on Morse Boulevard across the street from the Winter Park Train Station parking lot.

For more information, call 407-644-7207 or visit

No animals are allowed in Central Park or on Park Avenue between New England and Canton Avenues during Festival hours per Winter Park City Ordinance.