The 65th Annual Winter Park Sidewalk Art Festival is one of the nation’s oldest and most prestigious juried fine art shows. It consistently ranks among the most highly regarded outdoor art shows in the nation. In 2021, the festival was named #4 Best Show of All Times in Sunshine Artist’s national poll of All Time Favorites.

The show is located in historic downtown Winter Park, Florida, a beautifully landscaped area where artists' booths nestle under large oak trees throughout Central Park and stretch along Park Avenue. The three-day event takes place on March 15 - March 17, 2024, in the heart of this charming city, which is known for its brick streets, unique boutique shops, and inviting outdoor cafes and bistros. Attendance at the Festival is expected to reach over 250,000 people who will view the artwork of 212 artists and 3 emerging artists. One of Central Florida's largest annual outdoor events, the Festival also features a wide variety of entertainment on the stage in Central Park, food and beverage to please the whole family, a popular exhibit of student art from Central Florida schools, and many interactive arts for the kids.

A portion of the Festival's proceeds is donated to the Winter Park Sidewalk Art Festival Foundation to fund scholarships at Rollins College and University of Central Florida.