Winterset is a charming Iowa city with ties to Hollywood royalty
Winterset is the south-central Iowa city where John Wayne learned to walk and Clint Eastwood fell in love. This rural destination of about 5,400 is the birthplace of “The Duke,” who went on to Hollywood superstardom. “The Bridges of Madison County,” directed by and starring Eastwood, was filmed here. The John Wayne Birthplace Museum and Madison County’s world-renowned covered bridges are highlights of a community that blends history and small-town charm. “Winterset is friendly and welcoming,” says Marcia Munger of Keller Williams Realty, who grew up there and still regularly returns for visits with friends and family. “It’s a community with a lot of warmth and character.”
John Wayne museum, covered bridge fest are major tourist attractions
Winterset’s economy is boosted year-round by tourist dollars. “I don’t think I’ve ever gone back home and there isn’t someone taking a picture in front of the John Wayne statue,” says Munger of the iconic attraction at the corner of Washington Street and John Wayne Drive. The museum hosts an annual birthday celebration for its most famous resident every year in May. The community also hosts the two-day Covered Bridge Festival every year on the second full weekend in October. More than 150 vendors set up shop downtown, and the festivities include a parade and a classic car show. Madison County Regional Hospital in Winterset, and the Winterset Community School District are other top employers.
Historic architecture stands out among housing options
Winterset’s residential settings are typical of a small town in the 21st century. Most homes are older, with some built as far back as the 19th century. Colonial Revival and Victorian influences stand out among the older homes, which come in a variety of shapes and sizes and radiate out from the center of the community. Many historic homes have been renovated, adding curb appeal to walkable streets shaded by mature trees. “It’s a great place to grow up,” Munger says. “Kids will go off to college and work, then they have kids and will come back to raise a family.” Newer homes are contemporary models with driveways and attached garages in subdivision settings, primarily on the west side of the community. Homes on several acres or more can be found north of town. A small collection of townhouses can also be found. Prices range from under $100,000 to $500,000-plus. The median sales price is about $250,000.
Early winters forced a name change
Residents can expect summers to be hot and humid and winters to be cold and snowy. In fact, the community was originally named Summerset, until winter rolled around. Officials then changed the name. The community’s resilience was on display in the wake of a deadly tornado that swept through the Winterset area in 2022. “If a tragedy happens, everyone is there to help,” Munger says.
Covered bridge, tower featured attractions at historic City Park
City Park is filled with historical attractions, including Cutler-Donahue Covered Bridge and Clark Tower, a “castle” dedicated to the community’s early settlers. The walkable green space, which also includes a hedge maze, was placed on the National Register of Historic Places in 2021. Parts of the park were renovated after the 2022 tornado, and an all-inclusive playground was added in 2024. The community also boasts a soccer complex, a softball complex, youth baseball fields and a skate park. There’s even a pocket park dedicated to George Washington Carver. Boaters and anglers can take advantage of the recreational opportunities on nearby Cedar Lake. Lakeview Country Club offers 9 holes of golf along the lakefront.
Downtown still has an "old-time, small-town vibe"
Boutique shops, vintage stores and family businesses are concentrated near the Madison County Courthouse square in the heart of downtown. “It has an old-time, small-town vibe,” Munger says. “Montross Pharmacy is still just like it was when I was in high school in the ‘70s.” Restaurants, bars and cafes are also concentrated downtown, with several along the John Wayne Drive corridor. More shopping and dining options, including a pair of grocery stores, can be found north of downtown.
Four schools make up the local school district
Winterset Junior High, which earns a B from Niche, is the highest rated of four local schools. The junior high shares a campus with C-plus-rated Winterset Senior High, and nearby Winterset Middle has a B-minus. Winterset Elementary has a C-plus. Winterset High School offers dual-enrollment classes in English, math, science and social studies.
Easy access to Des Moines via nearby interstates
U.S. Highway 169 and Iowa Highway 92 intersect just north of downtown, providing convenient access to major interstates. Highway 169 connects directly to I-80, while Iowa 92 connects directly to Interstate 35. Both lead to the capital city of Des Moines, about 35 miles away. Winterset has a municipal airport, but Des Moines International is the closest commercial airport.
Written By
Matt Pallister
Photography Contributed By
Drew Davis
