Living in Winterset offers residents a sparse suburban feel and most residents own their homes. In Winterset there are a lot of parks. Many families and retirees live in Winterset and residents tend to be conservative. The public schools in Winterset are above average.

Winterset is widely known for its covered bridges. A total of six covered bridges are located in Madison County, including one in Winterset City Park. The annual Covered Bridge Festival celebrates the bridges and local heritage every second weekend in October.

Winterset is the county seat of Madison County. The population was 5,353 at the time of the 2020 census. The City resides at the intersection of US Highway 169 and Iowa Highway 92, while Interstate 80 and Interstate 35 are located within a 15 minute drive.