Winter Park Streets: Osceola Avenue Osceola Avenue is named after the lake it borders, which in turn was named after the Seminole Indian chief, Osceola.  Then Now This photograph is a view of Osceola Avenue east of a canal connecting Lakes Virginia and Osceola and was most likely taken during the first decade of the 1900's.  This was the only "run," as they were then known, not among the original natural drainage streams of Winter Park.  Fern Canal, as some call it, was first deepened by the owner of a saw mill on Lake Virginia so that he could float his logs through.  It was dredged in 1914 to make it passable. Osceola Avenue 2001.