The Winter Park Sidewalk Art Festival returns to Park Avenue celebrating 67 Years of Fine Arts and Crafts

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

The 67th Winter Park Sidewalk Art Festival takes place this weekend, with the three day event kicking off on Friday, March 20, and running through Sunday, March 22, 2026, with the streets of Park Avenue transformed into an outdoor gallery.

The festival features incredible artists from across the country, together with live entertainment, delicious food, and a weekend celebrating art in the heart of Winter Park.

This year's festival kicks off on Friday, March 20 with a concert featuring headliner Kim Waters, one of the premiere architects and reigning kings of Contemporary Jazz! 

Music starts at 3:30 pm at the stage in North Central Park, and the Jazz Concert starts at 5:30 pm with a lead in band, followed by Kim Waters at 7:30 pm. Music continues throughout the weekend too, featuring Orlando Children’s Choir, Lake Highland Hour of Darkness Jazz, The Hannah Stokes Band, Ella and The Bossa Beat and many more.

The Winter Park Sidewalk Art Festival is one of the nation’s oldest, largest and most prestigious outdoor art festivals, debuting 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 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 Source Book’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. In Art Fair Calendar's list of Best Art Fairs the festival ranks #6 in America and #1 in the South.

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.

Whether you’re a first time attendee ready to soak it all in or a seasoned collector with your patrons badge and wish list in hand, check out the 2026 artist lineup for the Winter Park Sidewalk Art Festival before you arrive in Central Park!

Start browsing now: https://www.wpsaf.org/artists/

Artists compete for 64 awards totaling $76,500. 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 is also a $2,000 annual “Monte Livermore Celebration of Nature Award”.

Plus, 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.

Kids can create their own artwork 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 festival features live music on Friday night. Taking place on the stage in North Central Park when the Winter Park Sidewalk Art Festival presents the 2025 Friday Night Concert. At 5:30 pm they open with the crowd-pleasing band, Brown Bag Brass Band, followed by George Porter Jr. & The Runnin’ Pardners starting at 7:30 pm.

For more details on this year's Winter Park Sidewalk Art Festival, click here.

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