Fredi Lexine

Winter Park Art Festival 2024 Lineup. The winter park sidewalk art festival is one of the nation’s oldest, largest and most prestigious outdoor art festivals. The winter park sidewalk art festival is held in the heart of beautiful winter park, florida.

March 21, 22 and 23, 2025. The groundhog may have seen its shadow weeks ago, but a local springtime tradition will return to park avenue on march 15, 16 and 17 with the 65 th annual winter park sidewalk art festival.