The Winter Park Sidewalk Art Festival is one of the nation's most prestigious outdoor art festivals, drawing artists and visitors from across the country to charming Central Park along Park Avenue.
What to expect: Hundreds of juried fine artists showcasing painting, sculpture, photography, jewelry, and more, plus live music, food, and family-friendly activities — all set among the oak-lined paths of Winter Park's iconic downtown. It's a can't-miss spring tradition and a showcase of one of Central Florida's most walkable, culture-rich communities.
Stroll, shop, and soak in the Park Avenue atmosphere. Plan your visit at the festival's official site.
Dates: March 20–22, 2026
Location: Central Park, Winter Park
