The 68th 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, with cash awards totaling $76,500 and dedicated Patron purchase funds expected to be over $100,000.  In 2025 the festival ranked #8 in the nation in Art Fair Sourcebook’s top fine art shows and in Sunshine Artist’s national poll of All Time Favorite Art Shows in 2021, the festival was named #4.

The show is located in historic downtown Winter Park, Florida, nestled throughout Central Park and stretching along Park Avenue. The event takes place on March 19 – March 21, 2027, in the heart of this charming city. Attendance at the Festival is expected to reach over 250,000 people who will view the artwork of 218 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 through the Jean Alice Oliphant Scholarship at Rollins College and The Winter Park Sidewalk Art Festival Scholarship at the University of Central Florida.