Winter Park Sidewalk Art Festival

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Winter Park Sidewalk Art Festival

The Winter Park Sidewalk Art Festival has been bringing fine art to Central Florida for 67 years!

The 68th Winter Park Sidewalk Art Festival will be held March 19, 20, 21, 2027. The Winter Park Sidewalk Art Festival is one of the nation’s oldest, largest and most prestigious outdoor fine arts & fine crafts festivals. Organized and run by a dedicated group of volunteers, the juried show is nationally recognized and is named the #5 Fine Art Show in the country by Sunshine Artist Magazine. The fe

stival features all original artwork that has been designed and executed by the exhibiting artists during the past two years. The show is conveniently located in Central Park, a beautifully landscaped area whose surrounding streets are closed during the festival to allow for foot traffic only. Many artist booths line Winter Park’s Park Avenue, the heart of a charming downtown with brick-lined streets, unique boutique shops, and multiple outdoor cafes and bistros. Attendance is expected to exceed 250,000 people for the three-day event. A panel of judges has selected 213 artists to participation this year.

08/24/2026

Thank you, Central Florida! We're honored to be voted runner-up for Best Festival in Orlando Weekly's 2026 Best of Orlando. Grateful for a community that shows up for local arts, year after year.

08/06/2026

Artist Applications are now open for the Winter Park Sidewalk Art Festival — one of the nation's oldest, largest, and most prestigious juried outdoor fine art festivals.

Artists have until September 23, 2026, to apply. This year's show offers $76,500 in cash awards and a projected $100,000 in Patron's Bucks, among the most generous purses in the country.

An independent panel of three nationally accomplished judges will select 218 fine artists and 3 emerging artists to exhibit on historic Park Avenue next spring, with an audience of approximately 250,000 art lovers over 3 days.

Applications close September 23rd; more information and the link to the application can be found here: https://www.wpsaf.org/info-for-artists/artist-application/

07/31/2026

CALLING ALL ARTISTS — applications for the Winter Park Sidewalk Art Festival open tomorrow, August 1st.

Coming into its 68th year, WPSAF is one of the nation's oldest, largest, and most prestigious juried outdoor fine art festivals -- and one of its most profitable! #8 in Art Fair SourceBook's 2025 rankings, #6 in Sunshine Artist's Top 200 (2010–2020), and #1 Best Festival in the South (Art Fair Calendar).

218 fine artists and 3 emerging artists will be selected by an independent panel of three nationally accomplished judges. $76,500 in cash awards. $100,000+ projected in Patron Bucks. $12,000 Best of Show purchase award.

Apply tomorrow through https://www.zapplication.org/

06/30/2026

The Winter Park Sidewalk Art Festival is a finalist for “Best Arts Event or Art Festival” in Orlando Weekly’s Best of Orlando 2026 competition! Voting is open now through July 15th, once per day, at vote.orlandoweekly.com

Your daily vote helps keep one of Central Florida’s longest running traditions in the spotlight!

04/20/2026

We are beyond honored that the Winter Park Sidewalk Art Festival caught the eye of Linnea Bailey and Southern Living. Thank you for shining a spotlight on our our vibrant community and the magic that happens every year right here in downtown Winter Park!

See why Winter Park, Florida is one of the South’s best train-friendly getaways, with a walkable downtown, family-friendly attractions, scenic boat tours, and easy car-free adventures just steps from the station.

03/30/2026

A huge thank you to our 2026 Entertainment Sponsor — Orlando Health and Orlando Health Jewett Orthopedic Institute!

Your support helped bring Kim Waters, Michael Andrew and Swingerhead, and other live entertainment to the stage last weekend. We are so grateful to have you in our corner, helping make the festival experience truly unforgettable for thousands of art and music lovers. Thank you!

Address

P. O. Box 597
Winter Park, FL
32790

Telephone

(407) 644-7207

Website

http://www.wpsaf.org/

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