Winside, settled in 1886, was originally located west of where the present town is and was called Northside. In 1882, the Chicago, St. Paul, Minneapolis, and Omaha Railroad constructed a line to the south, connecting Wayne to Norfolk.
After competing with the town of Northside, 3 miles to the southwest, the new town of Winside won the location of the railway's depot. The winning town captured the outcome in its name – Winside.
Winside currently has a population of about 468 people.