MAY 14-16, 2021
The 62nd Winter Park Sidewalk Art Festival

Where: In Central Park and along Park Avenue in Winter Park, FL

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. Festival. 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.



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.


The place to discover the talented artists of the next generation is at the Leon Theodore Schools Exhibit 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.