Winter Park Sidewalk Art Festival

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507 N New York Ave
Winter Park, FL 32789

The Winter Park Sidewalk Art Festival, one of the nation's oldest and largest outdoor art festivals, has been a significant community event since its inception in 1960. Organized by an all-volunteer board, the festival attracts over 250,000 visitors annually, showcasing a diverse range of artistic talent and promoting art appreciation within the community.

Beyond celebrating artists, the festival supports various programs focused on art education and outreach, including scholarships at Rollins College and the University of Central Florida. Through patron participation and donations, the festival continues to foster artistic engagement and create lasting memories for visitors and artists alike.

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4.522 reviews
Photo of Nancy W.
Nancy W.
3/27/2025

The Winter Park sidewalk art festival is a must-see if you're in the area during March. I've been to this festival several times And it seems to get larger as time goes on. Over a thousand...

Photo of Scott W.
Scott W.
3/25/2025

As art enthusiasts, my wife and I found this event to be a perfect experience, and I have to admit, I'm a bit embarrassed this was my first time attending. But rest assured, it won't be the...

Photo of Joseph H.
Joseph H.
6/16/2024

What an amazing event. This event is massive and stretches most of the historic downtown Winter Park. I spent most of the day browsing every tent and vendor. I love art so much and was so happy to...

Photo of Hideko M.
Hideko M.
3/23/2025

Please do not block off the vacant field for parking.... It was so packed on Saturday(all free street parking spots were taken...), and I had to park at "Event Parking" lot and costed me $20....

Photo of Alicia J.
Alicia J.
10/9/2023

This is such a fun weekend in Winter Park! My husband and I love making our way through Park Avenue and Central Park admiring the talented art displays and community booths. Many years ago we...

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