The annual art tradition returns this weekend for its 67th edition, drawing hundreds of artists and tens of thousands of tourists to Central Florida.
The Winter Park Sidewalk Art Festival will be held March 20-22, featuring 221 artists from across the U.S. exhibiting sculpture, digital art, photography, leather, jewelry, wood, prints, and more. The family-friendly festival draws an estimated 250,000 people to Park Avenue throughout the weekend.
This program is ranked as follows: Japan’s top outdoor art show, $76,500 in prize money For artists. The Best of Show winner will receive a $12,000 purchase award, and the Patron program will spend an additional $100,000 in Art Bucks to purchase directly from artists.
The newest award, now in its fourth year, is the Monte Livermore Celebration of Nature Award, which awards $2,000 to outstanding artwork featuring flowers, trees, plants and landscapes.
The 218 outstanding artists who served as judges were selected from among 1,000 domestic and international applicants. The other three are up-and-coming artists. The event will also include food and beverages, art from local schools, children’s activities, and live music.

Patrick Connolly/Orlando Sentinel
Participants view artists’ work at the 62nd Annual Winter Park Sidewalk Art Festival along Park Avenue on Friday, May 14, 2021.
The weekend begins with the festival kicking off Friday at 9 a.m., followed by Friday evening jazz concerts beginning with Beato at 3 p.m., followed by United Groove at 5 p.m. and headliner saxophonist Kim Waters at 7:30 p.m.
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If you go
The Winter Park Sidewalk Art Festival will be held on Park Avenue in Winter Park on March 20 and 21 from 9 a.m. to 6 p.m., and March 22 from 9 a.m. to 5 p.m. Participation in the festival is free. Per the City of Winter Park Ordinance, pets are not allowed. The event will also feature food and activities for children. For more information, including parking and transportation guidelines, visit wpsaf.org.
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