It was 1836 when Erastus Patterson, his wife Zeruah, and their five children joined a caravan of covered wagons from Vermont heading west. Stopping for the night on the wooded hill that is today called Lloyd Park, the Pattersons were enchanted with the area and decided to settle. They built a tavern, referred to today as the Patterson Tavern, for travelers along the Green Bay Trail from Fort Dearborn, Chicago to Fort Howard, Wisconsin. The first business in Winnetka was established.

Many other firsts were to follow. In 1854, in anticipation of the Chicago & Milwaukee Railroad Co. coming through Winnetka for the first time, Charles Peck and Walter S. Gurnee, president of the Railroad, created the original subdivision of Winnetka. Sarah Peck, Charles' wife, named the newly plotted village "Winnetka" after a Native American phrase meaning "beautiful land" she read in a book. (The source of this phrase has never been discovered.) Two years later, Sarah organized the first private school in Winnetka in a home on the northwest corner of Elm Street and Sheridan Road. A 15-year old teacher, living with the Pecks, instructed 17 pupils for $3.00 a week. The first public school was established in 1859. Known as District #2 School, the one-room structure sat on the present-day Village Green and held 25 students. It was forced to move ten years later when, in 1869, Charles Peck donated the Village Green to Winnetka for park purposes and stipulated that no structures ever be built on the land. The same year, Winnetka was incorporated as a village with a population of 450.