Winter Park Sidewalk Art Festival

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!

03/22/2026

It’s the last day of the Winter Park Sidewalk Art Festival, and the park is as beautiful as ever. Join us for one more stroll through incredible artwork, meet the artists, and find that piece you’ll wish you hadn’t left behind.

We’re open until 5 PM, so there’s still time to make it count.

03/22/2026

Announcing the 67th Annual Winter Park Sidewalk Art Festival award recipients!

🏆 Best of Show ($12,000 Purchase Award)
Chris Roll (Lakeland, FL) — “Awaiting Her Call” | Booth 161

✨ Edyth Bush Charitable Foundation Art of Philanthropy Award
Kristin Thorsen (Decatur, GA) — “Love It Or Lose It” | Booth 22

🎖 Morse Museum Award for a Distinguished Work of Art
Janvier Ngamije (Lewisville, TX) — Sweet Grass Basket | Booth 107

🌿 Monte Livermore Celebration of Nature Award
Douglas Piper (Greenville, SC) — “Fire Glow” | Booth 17

Explore the full list of 2026 winners: wpsaf.org/about/award-winners/

Congratulations to all of our award-winning artists and thank you to all of our festival artists for making the Winter Park Sidewalk Art Festival a destination for exceptional art.

03/21/2026

We’re open — and it’s another beautiful day in the park.

Stroll Park Avenue, explore incredible artwork, and be sure to stop by and see our volunteers, they’re ready to help you take home official festival posters and merchandise!

Sunshine, art, and a little something to remember it by. We’ll see you out here!

03/20/2026

Art may be the main event, but comfort matters too. Thank you to for keeping our festival guests cool, comfortable, and well cared for with their air-conditioned restrooms. We appreciate your partnership!

03/19/2026

The official program for the 67th Annual Winter Park Sidewalk Art Festival has arrived.

Explore the digital program and begin planning your weekend on Park Avenue: https://bluetoad.com/publication/?i=862199&p=1&view=issueViewer&pre=1

Thank you to our friends at Winter Park Magazine for bringing this year’s official guide to life.

03/17/2026

Art Heist in Progress…We’re diving into the archives (strictly authorized, of course) to uncover some of the most iconic vintage posters from the Winter Park Sidewalk Art Festival.

There are decades of design, bold colors, and a little bit of nostalgia to choose from, so we need your help:

Which years are you hoping to see? Let us know in the comments and you might just see your pick available at our merchandise tent at Park & Morse this weekend!

03/16/2026

Three Experts. Hundreds of Artists. Meet the judges selecting the award winners at the 2026 Winter Park Sidewalk Art Festival!

Each year, an independent panel of distinguished arts professionals reviews artist applications and select the artists for the show and later, the award winners. This process helps make our festival one of the most respected in the country.

This year’s judges bring decades of experience as artists, educators, curators, and arts leaders:

Thomas M. Brewer – Professor Emeritus of Art Education at UCF and nationally recognized art educator and ceramic artist.

Cheryl Strichik – CEO of the Monthaven Arts & Cultural Center and longtime arts advocate dedicated to expanding access to the arts.

Gina T. Washington – Multidisciplinary artist, educator, and cultural connector from Cleveland whose work and leadership span exhibitions, film, and arts organizations.

These three judges reviewed artist applications last fall and will walk the festival during the event to select this year’s award winners based on the overall quality of the artwork on display.

Learn more about our judges here:
https://www.wpsaf.org/about/judges/

03/14/2026

Less than ONE WEEK until the streets of Park Avenue transform into an outdoor gallery!

Join us March 20–22 for the 67th Annual Winter Park Sidewalk Art Festival featuring incredible artists from across the country, live entertainment, delicious food, and a weekend celebrating art in the heart of Winter Park.

Start planning your visit and explore this year’s artists, visit wpsaf.org or click the link in our bio!