When it comes to uncovering the heart and soul of Iowa, Winterset stands out in 2025 as the state’s most fascinating small town—rich in history, culture, and natural beauty. Tucked in the scenic countryside of Madison County, Winterset delivers authentic Midwest charm while offering unique attractions that make it a top destination for locals and travelers alike.
Covered Bridge Capital
Winterset is famously home to the romantic “Bridges of Madison County.” These iconic covered bridges, immortalized in both literature and film, date back to the late 19th century. Six distinct bridges, including the 104-foot Roseman Bridge, dot the lush landscape around Winterset, each providing picturesque views and a sense of nostalgia. October brings the lively Madison County Covered Bridge Festival, featuring more than 140 food and craft vendors, live demonstrations, and special events marking the 30th anniversary of the popular film adaptation.
Birthplace of John Wayne
Hollywood history buffs will be thrilled to find Winterset is the birthplace of legendary actor John Wayne. The John Wayne Birthplace & Museum—one of Winterset’s top attractions—is the only museum in the world dedicated to the Duke. Visitors can explore exhibits packed with rare artifacts, original movie scripts, vintage posters, and even one of Wayne’s custom-built cars.
Living History and Local Flavor
Winterset’s town square is anchored by beautifully preserved historic buildings, including the Romanesque Madison County Courthouse. The Madison County Historical Complex gives guests a glimpse of the region’s past, featuring the restored 1856 Bevington-Kaser House and a collection of vintage farm equipment and Civil War memorabilia. Winterset also boasts the Iowa Quilt Museum with rotating exhibits focused on the state’s quilting heritage.
For a taste of authentic Iowa, sample homemade apple fritters at Bakery Unlimited or enjoy a show at the multi-use Iowa Theater. Local favorites like The Drift serve up creative American fare and host game nights, while the Haynes Homestead pours mead cocktails and offers cheese platters in a cozy setting.
Festivals, Nature, and More
Nature lovers can explore Cedar Lake—perfect for hiking, paddling, and fishing—or wander through City Park with its noteworthy 25-foot limestone Clark Tower and a hedge maze. PepperHarrow Farm, just outside of town, kicks off summer with the annual Lavender Festival, inviting guests for al fresco dinners and workshops in floral design.
Winterset’s vibrant calendar also includes the Madison County Fair, the Festival of Lights, and weekly farmers markets running from May through October. Boutique shops, art galleries, and public murals make downtown strolls endlessly rewarding.
The Magic of Small-Town Iowa
What truly sets Winterset apart is its warm community spirit. Visitors are welcomed like old friends, and there’s always something new to discover—whether it’s a hidden hiking trail, a quirky local boutique, or a historical tidbit you’ll only hear from a town resident. With its blend of famous landmarks, cultural richness, annual festivities, and small-town hospitality, Winterset easily claims the title of Iowa’s most fascinating small town in 2025.
Sources
[1] https://www.smithsonianmag.com/travel/the-15-best-small-towns-to-visit-in-2025-180986681/
[2] https://www.worldatlas.com/cities/8-fairy-tale-small-towns-in-iowa.html
[3] https://khak.com/best-small-towns-iowa-midwest/
[4] https://realestate.usnews.com/places/rankings/best-places-to-live-in-iowa
[5] https://www.worldatlas.com/cities/6-most-overlooked-iowa-towns-for-2025.html
