Winter Park Sidewalk Art Festival

Application Deadline:

September 23, 2026

 

DON'T WAIT APPLY NOW!

 

"Be part of this highly acclaimed spring tradition in beautiful Winter Park, Florida"

MARCH 19, 20 & 21, 2027

Winter Park, Florida - Central Park & Park Ave

"Nationally recognized as one of the nation’s most profitable shows for artists!"

Be part of this widely acclaimed spring tradition in beautiful Winter Park, Florida. The Winter Park Sidewalk Art Festival is one of the nation’s oldest, largest and most prestigious juried outdoor fine art festivals. It’s also one of the nation’s most profitable. In 2024 the festival ranked #8 in the USA Today Readers’ Choice, 10 Best Art Festivals contest. And in 2025, ranked #8 In AFSB’s Best Fine Art and Best Fine Craft lists.

The festival debuted in March 1960 as a community project and is still produced today by an all-volunteer board that puts an emphasis on meeting the needs of the artists. Set in a beautiful, historic downtown setting, the festival draws approximately 250,000 art-loving visitors. Fine artists from around the world apply yearly to this highly competitive and very popular show. An independent panel of three judges will select the 218 fine artists and 3 emerging artists who will be invited to exhibit their works..

Applications Handled Through Zapplication

Cash Prizes:

Artists Amenities and Features:

Important Dates:

AWARDS - TOTAL OF $76,500

● Best of Show: Purchase Award, $12,000

● Edyth Bush Charitable Foundation Art of Philanthropy: Purchase Award, $5,000

● The Charles Hosmer Morse Museum Award for Distinguished Work of Art: $2,500

● The Monte Livermore Celebration of Nature Award, $2,000

● Ten Awards of Excellence: $2,000 each

● Twenty Awards of Distinction: $1,000 each

● Thirty Awards of Merit: $500 each

● In addition, Patron Program purchases are estimated to exceed $100,000 this year

● Artists’ Hospitality Center with refreshments – open daily from 8am – 4 pm 

● Limited free artists’ parking 

● Artist Housing Program 

● Booth sitting staffed by volunteers available on call 

● Artist Care Team – several visits each day 

● Saturday Night Artists’ Party (Dinner & Awards Presentation) 

● Art Festival Magazine distributed at event and archived on website 

● Artists’ Gallery on website 

● Security patrol after hours 

● Extensive media promotions throughout Central Florida leading up to and during the Festival 

● Artists retain all sales proceeds 

● Artist Helpline for the weekend of the festival

● Application Deadline: Monday, September 23, 2026

● Artist's Notification: November 3, 2026

● Festival dates: March 19, 20, 21, 2027

IMPORTANT FACTS TO KNOW ABOUT THE WINTER PARK SIDEWALK ART FESTIVAL

• Ranked #8 in the USA Today Readers’ Choice, 10 Best Art Festivals contest
• Ranked in the top 8 by Art Fair Source Book
• Great attendance with 250,000 expected over the three-day event
• Exceptionally large awards totaling $76,500 including $12,000 Best of Show purchase award
• Additional dedicated patron purchase funds projected to be over $95,000
• Emerging Artist Program for Florida Artists
• Image Review Workshop

$45.00 JURY FEE - $575.00 BOOTH FEE

WHAT DO PREVIOUS ARTISTS HAVE TO SAY ABOUT THE FESTIVAL AFTER PARTICIPATING...

Exhibitor Comments From Previous Years

"It was my best fair ever! And the weather was perfect."

"Much better than all the other festivals. Awesome staff, security, and volunteers." 

"Winter Park is always one of my best earners." 

"It’s such a pleasant area, making for a great experience." 

"The Winter Park Sidewalk Art Festival is top on my list!" 

"The Hospitality Tent exceded my expectations."

"I felt my stuff was safe all weekend. That is my main priority."

"It was my first year and it was a amazing experience!"

"Best show for sales ever for me. Thanks!" 

"The community was very supportive." 

"Best sales I've ever had at any art show since 1977!!!" 

"Impressed by how well run the show was and the high caliber of art." 

"Everything was excellent from start to finish!" 

"We LOVE this art festival ... our favorite show of the year."

"Loved it! Everyone, management, staff and volunteers were all wonderful as usual! Thank you!"

"The volunteers are fantastic. Providing water and snacks helps get through the long days!!"

"The buyers were so engaged, the setting was very pleasant and the show is very well run."

"Good set up, lots of artists, easy food nearby and at the festival, the patron bucks are amazing, I will be devastated if I do not get back in again!!!! "

"I sold more art here than any other show I have ever done. Very happy with the show and how it was managed."

"Easily one of the best festivals I have participated in. You all really care about artists!"

"Great show, friendly volunteers, wonderful location, love the spacing between tents."

"It was my first year being accepted after applying for years. I will definitely apply again!!"

"We love this festival - so very well organized and wonderful hospitality and attendees!"

"We loved the Artist Care Team. The water and snacks brought to the artists were greatly appreciated"

The Winter Park Sidewalk Art Festival

PO Box 597 Winter Park, FL 32790-0597

(407) 644-7207

wpsaf@wpsaf.org

FESTIVAL CONTACT INFORMATION

            ● Voice message system (No Texting): 407-644-7207

            ● Website: www.wpsaf.org

            ● Application questions: zapp@wpsaf.org

            ● General questions: wpsaf@wpsaf.org

            ● Artist Questions: zapp@wpsaf.org

            ● Emerging artists: ea@wpsaf.org