MARCH 21 - 23, 2025


65th Winter Park
Sidewalk Art Festival
March 15 - 17, 2024
Congratulations to All Award Winners, Including Our Best of Show!


Best In Show
Matheson Hammock Park

Artist: Hernan Rodriguez

Judges Statement:

"While we appreciate the high degree of realism, it is sensitively painted in a way that goes beyond just technical achievement.  We are impressed by the sense of depth and space and subtle attention to design and composition.  The artist is able to guide us from the observation of the rocks lying beneath the transparent shallow water, to the deeper space that leads us to the other shore.  The painting is striking both when viewed from a distance, seeing the overall composition, as well as in closer observation of the paint handling and surface.  The greatest strength of the work is its sense of space.  This is a difficult thing to achieve.  The artist has fully captured this moment by the water.  The painting invites us to step into it, but it also makes us pause to contemplate what the artist has achieved."


Click Below to Learn More About This Year's Winners!


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 2024 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. The majority of your funds stay with you to purchase art and the remainder goes to support The Winter Park Sidewalk Art Festival.

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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. 

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2024 Award Winners

"Matheson Hammock Park"
Painting by Hernan Rodriguez


"Taking the Backroad"
Drawing and Pastels by Wonda Granville


"Meadow View"
Painting by David Skinner

2024 Entertainment Sponsor
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