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62nd Annual Winter Park Sidewalk Art Festival at Central Park, Winter Park [Free]
May 14 - May 16
The annual event is one of the nation’s oldest, largest, and most prestigious outdoor fine arts & fine crafts festivals. It’s produced by an all-volunteer board and draws up to 350,000 visitors each year
It is free to attend. Hours are 9am-6pm on Friday and Saturday and 9am-5pm on Sunday.