During my road trip through Iowa, I made a stop in the small town of Winterset. Despite having only a few thousand residents, Winterset has a classic town square surrounded by shops and historic buildings. Walking around the center of town felt like stepping into the kind of small Midwestern community I had imagined before coming to Iowa.
At the center of the square is the Madison County Courthouse, an impressive building that dominates the surrounding downtown. The courthouse and businesses arranged around it give Winterset a very traditional town layout, and much of the historic character of the area has been preserved.
Around the downtown square I also came across several large vintage photographs showing scenes from Winterset’s past. I didn’t find much information accompanying the particular photographs I saw, but they added to the historic atmosphere of the town. Winterset itself was established in 1849 and has managed to retain much of its small-town character more than a century and a half later.
Many of the businesses around the town center seemed to specialize in furniture, antiques, and home decorating. I happened to visit on a Sunday, so most of them were closed, although I probably wasn’t going to do much shopping anyway. I was there at the beginning of September when it was still hot and dry outside, which made it a little strange to already see autumn and Halloween decorations appearing in the windows.
The early Halloween displays were another little detail I remembered from walking around Winterset. Even though the weather still felt like summer, the shops were already preparing for fall. With the older storefronts surrounding the town square, the decorations fit the atmosphere surprisingly well.
What originally brought me to Winterset was its connection to John Wayne. I hadn’t known before traveling through Iowa that the famous actor was born here, but once you’re in town it’s difficult to miss the connection. One of the main streets carries his name, and references to John Wayne can be found throughout Winterset.
I actually discovered John Wayne’s connection to Winterset by accident after seeing a sign pointing toward his birthplace. I initially assumed he had spent much of his childhood here, but he was born in this small house in 1907 and moved with his family to California while still a young child. The house has been preserved as part of the John Wayne Birthplace & Museum, giving visitors a chance to see where the future Hollywood star’s life began.
Outside the museum stands a statue honoring John Wayne and his long film career. Although his time living in Winterset was brief, the town clearly takes pride in being his birthplace. What began as an unplanned stop after spotting a roadside sign ended up giving me one of the more memorable small-town experiences from my trip across Iowa.
