Winter Park Sidewalk Art Festival™ 68th 2027

Overview

The 68th Annual Winter Park Sidewalk Art Festival is one of the nation's oldest and most prestigious juried fine art shows. Ranked #8 in the nation in 2025 by Art Fair SourceBook, it features 218 artists and 3 emerging artists over a three-day event in historic downtown Winter Park, Florida. Expected attendance exceeds 250,000. A portion of proceeds benefits scholarships through Rollins College and the University of Central Florida.

Key Dates

• August 1, 2026: Application available on ZAPP
• September 23, 2026: Application deadline by Midnight, EST
• November 3, 2026: Notification of screening results emailed on or before this date
• December 7, 2026: Acceptance and Exhibitor/Booth Fee due by Midnight, EST
• December 31, 2026: Exhibitor/Booth Fee refund request deadline
• March 18-19, 2027: Artist setup
• March 19-21, 2027: Festival hours - Friday & Saturday 9am-6pm, Sunday 9am-5pm

Eligibility & Requirements

Must be at least 18 years of age. Artwork must be substantially the same as shown in submitted images; non-compliance may result in expulsion from the show. Previous WPSAF award-winning artwork is not eligible for awards. The festival is family-oriented; artwork featuring nudity must portray the human body in a respectful and non-exploitative manner.

Application & Submission

• Four images required: three of current artwork completed in 2020 or after with no signatures or initials, and one booth image with no distracting or identifying markers such as signage, booth cards, and people
• Each artwork image must show the year created on the application (not on the image itself)
• May submit applications in up to three different categories, but only two entries may be accepted
• Artists may apply only once in a category
• Screening order established by date application is marked 'Received' in ZAPP

Fees

Application fee is $45.00 (non-refundable). Exhibitor/Booth Fee due by December 7, 2026. Refund requests accepted through December 31, 2026, subject to a $35.00 administrative fee.

Awards

• 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

Judging Process

Three independent judges selected from across the country will review digital images in October to select festival and waitlist artists. The same judges will review exhibited work in March to determine award eligibility based on overall quality. Artists select one piece for Saturday's awards processing that best represents their entire body of work.

Artists' Amenities

• Artists' Hospitality Center with refreshments (open daily 8am-4pm)
• Limited free artists' parking
• Artist Housing Program
• Booth sitting staffed by volunteers available on call
• Artist Care Team with several visits each day
• Saturday Night Artists' Party with 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
• Artists retain all sales proceeds
• Artist Helpline for the festival weekend

Contact Information

• Website: www.wpsaf.org
• Voice: 407-644-7207 (no texting)
• Application questions: [email protected]
• General questions: [email protected]
• Artist Questions: [email protected]
• Emerging artists: [email protected]
• Mailing: P.O. Box 597, Winter Park, FL 32790-0597