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The 64th Winter Park Sidewalk Art Festival kicks off with jazz stars Spyro Gyra

Updated: Feb 29

Launched in 1960, the Winter Park Sidewalk Art Festival is one of the oldest, largest and most prestigious outdoor art festivals in the country and attracts up to 350,000 visitors each year.

This years festival takes place from Friday, March 17 to Sunday, March 19, 2023

Taking place in Central Park and along Park Avenue in Winter Park. the free to browse show features hundreds of national artists displaying paintings, sculpture, glasswork, jewelry, woodworking and much more.

This years festival will feature a kick-off event leading up to festival weekend!

This Saturday, Saturday, March 11, an extra special jazz concert will take place in Central Park.

Jazz superstars Spyro Gyra will perform live in Central Park from 7:30 pm to 9 pm.

The evening will also feature Lake Highland Jazz Band from 3 pm to 4 pm,. and the Tal Cohen Trio from 5 pm tp 6 pm.

Everyone is invited to bring blankets and a picnic, with spots available on the lawn from 12 pm.

The 64th Winter Park Sidewalk Art Festival kicks off with Jazz stars Spyro Gyra

Music Schedule:

Saturday, March 11 3:00-4:00 Lake Highland Jazz Band 5:00-6:00 Timucua presents The Tal Cohen Trio 7:30-9:00 SPYRO GYRA

Additionally, during the three days of the festival there will be soft, contemporary music at the stage in North Central Park.

Friday, March 17 3:00-4:00 Flint Blade 4:30-6:00 Dana & Sharon Saturday, March 18 10:30-11:30 Suzuki Institute 12:00-12:30 Orlando Children's Choir 1:00-1:30 Paige Keiner 1:45-2:30 Cat Ridgeway 3:00-4:00 Patchouli 4:45-6:00 Greg Seel & Soul Purpose March 19 Sunday 10:30-11:30 Paint it Black 12:00-12:30 Arts 4 All presents - TBA Timicua Presents: 1:00-1:45 Don Soledad Group 2:15-3:00 Gerald Law and the Clutch 3:30-4:45 April Brown and the After 5 Band

Winter Park Sidewalk Art Festival

This years festival amazing 2023 poster artist, Debo Groover (left) visited Winter Park last week and met with WPSAF Co-Presidents Jennifer Clark and Greg Witherspoon for an afternoon of poster signing.

Response to this year's poster has been fantastic, purchase yours at the festival March 17, 18 and 19.

Posters are available after the festival by mail. See the Store tab on our website:

The 64th Winter Park Sidewalk Art Festival

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

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.

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. New in 2023 is a $2,000 annual “Monte Livermore Celebration of Nature Award”. 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.

Winter Park Sidewalk Art Festival

For the younger artists, girls and boys 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.

Winter Park Sidewalk Art Festival

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