At the turn of the century, Lakeside was home to some of the most famous Lake Michigan lakeshore resorts. Lakeside's history, like its Harbor Country sister towns, began with logging that fed nearby Chicago's insatiable need for lumber. Farming soon replaced the disappearing forests to keep the land lush and green. This rural lakeshore location fostered the next economic chapter as a popular vacation destination for nearby Chicagoans beginning in the early 1920s.