Melissa Donovan
One of the most distinguished outdoor art festivals in the United States is set to return this March. The Winter Park Sidewalk Art Festival, a highly anticipated cultural event, is marking its 66th year as a premier fine arts showcase. With its origins dating back to 1960, this juried festival continues to attract both emerging and established artists, making it a must-visit for art enthusiasts.
March 21-23, 2025
- Friday & Saturday: 9 a.m. – 6 p.m.
- Sunday: 9 a.m. – 5 p.m.
- Location: Central Park & Park Avenue, Winter Park, Florida
A Top-Ranked Art Festival
The Winter Park Sidewalk Art Festival has garnered national acclaim for its artist-friendly atmosphere and impressive sales opportunities. It ranks #3 in Art Fair SourceBook’s 2020 listings and #6 in Sunshine Artist’s Top 200 art shows from 2010-2020. Additionally, it has been recognized as #1 Best Festival in the South by Art Fair Calendar and was recently voted the #3 All-Time Favorite Festival in a national survey by Sunshine Artist.
An Artistic Extravaganza
Each year, approximately 250,000 visitors attend the festival to enjoy a diverse range of artwork, including painting, photography, sculpture, jewelry, digital art, mixed media, and more. A total of 212 artists, selected by a panel of nationally recognized judges, will exhibit their works. In addition, three emerging artists will have the opportunity to showcase their talents and gain exposure.
Prestigious Awards and Cash Prizes
Artists will compete for $76,500 in cash awards, one of the highest prize pools in the country. The Best of Show award offers a $12,000 purchase prize, with the winning piece becoming part of Winter Park’s permanent collection. Other notable awards include the $5,000 Art of Philanthropy Purchase Award, the $2,500 Distinguished Work of Art Award, and the $2,000 Monte Livermore Celebration of Nature Award. Additional Awards of Excellence, Distinction, and Merit further recognize outstanding artists. An estimated $90,000+ in Patron Bucks will also be available, enhancing artist sales.
A Festival Beyond Art
Beyond the extraordinary artwork, attendees can enjoy live music performances, a diverse food court, and entertainment throughout the weekend. Families can take advantage of the Children’s Workshop, offering free hands-on art activities, and the Leon Theodore Schools Exhibit, showcasing the talent of Orange County’s young artists.
Festival Merchandise & Visitor Information
Festival-themed T-shirts, posters, and memorabilia will be available at designated merchandise tents. A complimentary bike corral is available for visitors arriving by bicycle.
For health and safety, handwashing stations and sanitizers will be available. No pets (except certified service animals) are allowed in the festival area per city ordinance.
For additional details, visit the festival website or call 407-644-7207.
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