Lena-Winslow High School, dedicated December 7, 1958 and affectionately known as "Le-Win", is a high school located in the town of Lena, Illinois. Part of the Lena-Winslow Community Unit School District, Le-Win became the third largest school district in Stephenson County, when, in 1949, the State of Illinois mandated that larger school districts be created. Only the districts of Dakota and Freeport are larger.