Get your paintbrushes ready — Winter Park is calling! The Winter Park Sidewalk Art Festival has announced the dates for its 68th edition: March 19, 20 and 21, 2027. Central Park and the charming Park Avenue will once again turn into a giant open-air gallery, from 9 a.m. to 6 p.m. on Friday and Saturday and 9 a.m. to 5 p.m. on Sunday.
It is one of the oldest, largest and most prestigious outdoor art festivals in the United States. It debuted in March 1960 as a community project bringing local artists and art lovers together, and today it is run entirely by volunteers and welcomes up to 250,000 visitors each year. More than a thousand artists from around the world apply for a spot, and an independent panel of three judges selects the exhibitors. It consistently ranks among the top juried fine-art festivals in the country — number one in the South according to ArtFairCalendar.
The festival spans fine arts and crafts in categories like clay, glass, jewelry, painting, photography, sculpture, watercolor, wood and more, with 64 awards totaling $76,500 on the line. The little ones get their own creative space too: the Children’s Workshop offers free hands-on art activities from 10 a.m. to 4 p.m. all three days, and the Leon Theodore Schools Exhibit showcases artwork by thousands of Orange County students. Add live music on the stage in north Central Park, a free bike corral, and the festive atmosphere of Park Avenue — spring in Winter Park is going to be pure art.
Photo: Miosotis jade / Wikimedia Commons (CC BY-SA 4.0)
