FESTIVAL: MARCH 17-19, 2023

64th Winter Park
Sidewalk Art Festival
Festival: March 17 - 19, 2023
Concert: March 11, 2023
Stay Tuned for Details About the National Music Headliner at the Bandshell!


Monte Livermore Award

The Winter Park Sidewalk Art Festival is excited to announce a new art award with the establishment of “The Monte Livermore Celebration of Nature Award”, for presentation in 2023 and every year thereafter. This $2,000 annual award is made possible by a generous donation from family members Phyllis L. and Fred K. Smith, Laura and Taylor C. Smith, Tammy Smith White and Thomas F. White honoring the memory of Robert Montbriand Livermore, Jr. (Monte).


The award will recognize a distinguished work of art, in any medium, that “Celebrates Nature”. Monte was a beloved Winter Park horticulturalist, owner of a boutique nursery & garden center named Bocelli, and a dedicated WPSAF Board Member, past festival Co-President, past festival Foundation Board Member and enthusiastic art patron. The winning artwork should reflect a love of nature with an emphasis on flowers, plants, trees or landscapes.


The first award recipient will be selected from the 2023 Winter Park Sidewalk Art Festival artists by the Official WPSAF Judges and will be one of The Festival’s prestigious top 4 awards. We are honored to announce that the first award presentation will be made by Laura and Taylor C. Smith at the Artists’ Party, Saturday night, March 18, 2023.


The Festival’s awards purse ranks among the largest at the nation’s top shows. This award brings the new total to $76,500. Plus, the Patrons Program is expected to spend over $85,000 in Art Bucks this year.
Click below to learn more about the Artist Awards for 2023.


To Beautiful Park Avenue In Winter Park

The Winter Park Sidewalk Art Festival is one of the nation’s oldest, largest and most prestigious outdoor art festivals. The Festival debuted in March 1960 as a community project to bring local artists and art lovers together. It is produced by an all-volunteer board and draws more than 250,000 visitors each year. 

Learn More
Introducing the 2022 Festival Poster!
Be A Part Of The Festival

By volunteering you will experience a one-of-a kind behind-the-scenes opportunity to gain a deeper appreciation for the artists and their award-winning artwork. Our volunteers help make the Winter Park Sidewalk Art Festival one of the top outdoor festivals in the country.

Volunteer Now
Support the Festival

Our Patrons Program was created to provide support of Festival artists through dedicated funds pledged to purchase artwork during our annual show. By participating, Patrons make monetary pledges for given levels of spending. Up to 95 percent of your contribution stays with you to purchase art and the remainder goes to support The Winter Park Sidewalk Art Festival.

Visit Patron Page
Support Our Foundation

Since 1960, The Winter Park Sidewalk Art Festival has been a community leader in bringing art and the community together and has created wonderful memories for its visitors through the years. Donations to the foundation will help finance programs created to promote art appreciation and education through children’s programming at the annual Winter Park Sidewalk Art Festival, our scholarship programs at Rollins College and University of Central Florida and other community outreach programs throughout the year. 

Donate Now
2022 Award Winners

"Internal Structures"
Sculpture by David Figueroa


"Under Lock & Key"
Metal by David Vigo


"Jesus Saves"
Painting by Matthew Cornell

2023 Featured Sponsors
View All Our Sponsors
In Central Park and Along Park Avenue in Winter Park, FL
9 a.m. – 6 p.m., Friday and Saturday; 9 a.m. – 5 p.m., Sunday
(407) 644-7207