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Three-Day Winter Park Sidewalk Art Festival returns this weekend to celebrate its 65th year

Every year approximately 350,000 visitors attend the Winter Park Sidewalk Art Festival, regarded as one of the best arts festivals in the country.

Winter Park Sidewalk Art Festival

One of Central Florida’s most anticipated arts festivals will celebrate its 65th year, with the Winter Park Sidewalk Art Festival returning on March 15, 16, 17, 2024.

The festival is one of the nation’s oldest and most prestigious juried fine art shows. It consistently ranks among the most highly regarded outdoor art shows in the nation.

The show is located in the heart of Winter Park, Florida, a beautifully landscaped area whose surrounding streets are closed during the Festival to allow for foot traffic only.

Artists’ booths nestle under large oak trees in Central Park and line Winter Park’s historic Park Avenue, a quaint and charming downtown area with brick streets, unique boutique shops, and inviting outdoor cafes and bistros.

Winter Park Sidewalk Art Festival

Artists compete for 64 awards totaling $76,500. The festival donates the winning work to the City of Winter Park, and all are on permanent display at the Winter Park Public Library.

More than 1000 artists from around the world applied for this year’s event. An independent panel of three judges then selected the artists that will exhibit their works. at this year's festival.

The festival will include 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.

In addition to the art on display, the festival includes free entertainement throughout the weekend, with the festival kicking off on Friday with the Friday Night Concert in North Central Park. The years concert features a tribute to the late Jimmy Buffet starting at 5:45 pm with the crowd-pleasing band, Landsharks, followed by the jazzy headliner Michael Andrews and Swingerhead starting at 7:30 pm.

The festival also includes its of fun for the kids 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 am - 4 pm on Friday, Saturday and Sunday. Easel painting is from 10 am - 3 pm on Saturday and Sunday.

Winter Park Sidewalk Art Festival


The Winter Park Sidewalk Art Festival is one of the nation’s oldest, largest and most prestigious outdoor art festivals. It’s produced by an all-volunteer board and draws up to 250,000 visitors each year.

The festival consistently ranks among the top juried fine-art festivals in the country.  National accolades include # 3 in Art Fair SourceBook’s 2020 festival rankings and # 6 in Sunshine Artist’s Top 200 from 2010-2020, a 10-year ranking of the nation’s most profitable art shows, plus in ArtFairCalendar's list of Best Art Fairs the festival ranks # 6 in America and # 1 in the South.

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Winter Park Sidewalk Art Festival

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Emma Walton News Producer

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