MARCH 18-20, 2022
The 62nd Winter Park Sidewalk Art Festival

Where: Central Park and along Park Avenue in Winter Park

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’s produced by an all-volunteer board and draws up to 350,000 visitors each year. More than 1,100 artists from around the world applied for this year’s event. An independent panel of three judges selected the artists exhibiting their works. The festival consistently ranks among the top juried fine-art festivals in the country. National accolades include the No. 3 ranking in Art Fair Source Book’s “Fine Art Events,” the No. 6 ranking in Art Fair Calendar’s “2019 Best Art Fairs,” the No. 1 ranking in Art Fair Calendar’s “Best Southern Art Fairs” and the No. 6 ranking in Sunshine Artist Magazine’s “Top 100.”

For the first time since 1960, the 2020 festival was canceled as the COVID-19 pandemic was spreading across the nation. A year later, the 2021 festival, originally scheduled for March 19, 20, 21 was postponed until May 14, 15, 16, allowing more time for the public to become vaccinated and creating a safer environment for this outdoor event.  



About The Festival


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


Artists compete for 63 awards totaling $74,500. The Best of Show purchase award was increased in 2019 to $12,000. The festival donates the winning work to the City of Winter Park, and all 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, while 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.


Traditionally the festival features a very popular Friday night concert and music throughout the festival’s three-day run at the stage in north Central Park.  This year the Friday night concert has been cancelled due to COVID-19 virus guidelines about social distancing at this usually crowded sit-down event.  There will be some light entertainment throughout the weekend at various locations throughout the park.


Winter Park Sidewalk Art Festival T-shirts and other memorabilia are available at three merchandise sales tents. The tents are located at the south entrance (Park and New England avenues), at the center intersection (Morse Boulevard and Park Avenue), and at the north entrance (Park and Garfield avenues). Posters will be sold at the three merchandise tents, while a vintage poster tent merchandise tent will be located across the mulch path next to the festival headquarters at Park Avenue and Morse Boulevard.

Vintage t-shirts will be on sale on Morse Blvd. near the beer garden.  This year’s vibrant and whimsical poster is a mixed-media collage called Flamingos and Friends Exploring Winter Park by popular local artist Victor Bokas. After the festival is over, you can still purchase this year’s poster — and past posters — by visiting the festival’s website at


Due to the COVID-19 virus and to provide room for social distancing for the artists’ booths, there will be no easel painting at the 2021 festival. The Children’s Workshop was moved to our virtual festival that was held March 15 through March 31. Twelve museums and learning centers participated with on-line art demonstrations and project kits that could be picked-up at the stage in Central Park on Saturday, March 15. These demonstrations will still be available on-line during our live festival and can be accessed through out website at


The live schools exhibit was also cancelled for the 2021 festival, but was moved to our virtual festival that was held in March. The amazing artwork of students from 87 Orange County public and private schools was on display and middle and senior high school art was judged for awards. The winners list and the student entrees can still be seen by going to our virtual festival site available through our website at The virtual site was created on the Eventeny platform.


Ride your bike to the festival and park it at the free Bike Corral provided by the Winter Park Pedestrian and Bicycle Advisory Board. The corral is located off Morse Boulevard across the street from the Amtrak Station parking lot.

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

No animals are allowed (except certified service animals) in Central Park or on Park Avenue between
New England and Canton Avenues during festival hours, per a City of Winter Park Ordinance.

Visitors are asked to follow current COVID-19 CDC guidelines. Although no longer mandated by the state, face masks/coverings are encouraged to be worn for the protection of yourselves and others at your comfort level. Keep a safe social distance from others, avoid standing in crowded areas and wash your hands frequently. Hand washing stations and sanitizer will be available throughout the park.