Three days of art, sunshine and people-watching return at the 67th annual Winter Park Sidewalk Art Festival takes over downtown Winter Park. One of the nation’s oldest outdoor art fests will transform Central Park and surrounding Park Avenue into a sprawling open-air gallery featuring hundreds of artists from around the country.
More than 1,000 artists applied to participate this year, with work on display spanning sculpture, painting, photography, jewelry, glass, fiber art, mixed media and more. Beyond the booths, the festival features live music in Central Park and a free Children’s Workshop hosted by local museums and art centers.
Attendees can also explore the Leon Theodore Schools Exhibit, showcasing thousands of pieces created by Orange County students — a celebration of our city’s next generation of artists.
Friday-Sunday, March 20-22, Central Park, North Park Avenue and West Morse Boulevard, Winter Park, wpsaf.org, free.
Orlando’s daily dose of what matters. Subscribe to The Daily Weekly.
Related Stories
The Baker’s Son in Kissimmee is proof that good bread runs in the family
‘Incoherent’: DeSantis slams sheriffs’ pushback on deporting undocumented immigrants
Fandom explosion MegaCon is back in Orlando, this time with the singular Mr. T
This article appears in March 18-24, 2026.