Last Updated on November 18, 2022
This year the Winter Park Sidewalk Art Festival is celebrating its 62nd year! The outdoor art festival is one of the nation’s oldest, largest, and most prestigious, and it happens to be located in the heart of beautiful downtown Winter Park, Florida.
The festival, which made its debut in March 1960, helps bring together local artists and art lovers. In the past, the festival has drawn more than 350,000 visitors over the course of the three day event! In 2021, the first-ever virtual festival was held. The live festival was rescheduled from March to May 14-16 to allow more time for the public to become vaccinated and create a safer outdoor environment.
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
About the Festival
CATEGORIES
You can view a wide array of arts at the festival including clay, digital art, drawings, pastels, fiber, glass, graphics, printmaking, jewelry, leather, metal, mixed media-2D, mixed media-3D, painting, photography, sculpture, watercolor, wood, and more!
AWARDS
The artists attending the festival will also be competing for a total of 63 awards with prize money totaling $74,500. The winning work of art is donated to the City of Winter Park, and you can view the display at the Winter Park Public Library.
MUSIC AND ENTERTAINMENT
While the festival generally has a Friday night concert, this year’s concert has been canceled due to COVID-19 social distancing concerns. However, there will be entertainment spread throughout the weekend in multiple locations in the park.
MERCHANDISE
If you’re looking to purchase merchandise from the Winter Park Sidewalk Art Festival, T-Shirts, posters, and other memorabilia are available at three different merchandise sales tents throughout the festival.
We are partial to the poster this year since it features our favorite Florida bird – the flamingo! The poster, called Flamingos and Friends Exploring Winter Park, was created by local artist Victor Bokas.
Make sure to also check out the 2021 Festival Map!
Before you visit, check out Seven Reasons to Fall in Love with Winter Park.