Winter Park Sidewalk Art Festival

09/16/2026

Attention Artists! One week remains to apply for the 68th Annual Winter Park Sidewalk Art Festival, taking place March 19–21, 2027, in historic downtown Winter Park.

We're especially eager to hear from Florida artists just beginning their careers. Our Emerging Artist Program, running since 1997, selects three artists for a fee-free festival debut -- administrative and exhibitor fees waived, lodging provided, and a place in one of the nation's most highly regarded outdoor art shows.

All artists: applications close September 23rd, midnight EST, through ZAPP. Emerging artists should apply under the Emerging Artist category using code EA68.

https://www.wpsaf.org/info-for-artists/artist-application/

09/14/2026

Did you know? Since 2008, the Winter Park Sidewalk Art Festival Foundation has been nurturing young artists across Central Florida.

Each year, more than 1,000 children pick up a brush for easel painting at the Festival, and museum workshops welcome over 500 kids a day for hands-on art activities. Through the Leon Theodore Schools Exhibit, 4,500+ Orange County students see their artwork showcased -- often for the very first time. The Foundation also funds scholarships at Rollins College and UCF, helping the next generation of artists go further. Art appreciation starts young, and your support makes it possible!

Learn more at wpsaf.org/about/foundation/

09/10/2026

Less than two weeks remain to apply for the 68th Annual Winter Park Sidewalk Art Festival -- one of the nation's most prestigious juried outdoor art shows, taking place March 19–21, 2027, in historic downtown Winter Park, Florida.

With $76,500 in cash awards, Patron purchase funds expected to exceed $100,000, and over 250,000 expected attendees along Park Avenue and throughout Central Park, this is a show worth carving out time for.

Applications close September 23rd. We hope to see your work on the Avenue!

08/29/2026

Applications are now open for the 68th Annual Winter Park Sidewalk Art Festival, taking place March 19-21, 2027 in the heart of historic downtown Winter Park.

For almost seven decades, this festival has brought artists and collectors together throughout Central Park and along Park Avenue - and it remains one of the most highly regarded outdoor art festivals in the country. Ranked number 8 nationally by Art Fair Sourcebook, with more than $76,500 in cash awards and patron purchase funds expected to exceed $100,000 again in 2027!

Applications close September 23rd, learn more: https://www.wpsaf.org/info-for-artists/artist-application/

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!