The journey to Darlington Country Club begins at either Madison's Dane County Regional Airport, roughly an hour's drive southwest, or Chicago's O'Hare, which sits about two and a half hours to the east. The route from Madison traces Wisconsin's gently rolling farmland through Lafayette County, where the landscape softens into pastoral hills and quiet dairy country. As you approach Darlington - a small town tucked into the state's southwestern corner - the roads narrow and the pace slows, offering a genuine retreat from urban corridors into a corner of Wisconsin where golf remains refreshingly unhurried and community-rooted.