The pioneering and developing of Oconomowoc began in 1837 when the first white man, Charles Sheldon, came to this area to build his log cabin. He found that the Potowatomi Indians had already laid the foundation of what they called Coo-No-Mo-Wauk (where the waters meet, or river of lakes), which in time would become Oconomowoc.

As the town grew and word of its beauty and natural wealth spread, tradesmen began to arrive. One such early settler was a young man by the name of John S. Rockwell. He built the grist mill, owned the first store and hotel, and donated sites to all the churches. He started the fire department, the library, the elementary school and a young ladies seminary called Bord du Lac. His stout heartedness and ingenuity earned him the title "Father of Oconomowoc."

Fueled by its growing reputation, Oconomowoc entered a new era marked by the title "Newport of the West." This era began in the 1870s and continued into the 1930s. Lured by Oconomowoc's great beauty, families of wealth from Chicago, St. Louis and Milwaukee crowded its lake shores with palatial, colonnaded country mansions and lavish landscapes. At one time, Lake Road was referred to as Presidents' Avenue since Taft, Grant, Cleveland, Coolidge, McKinley and Teddy Roosevelt had visited and enjoyed famous Draper Hall and the hospitality of its wealthy residents.