Best Things to do in Winterset, Iowa: From Covered Bridges to Small Town Fun
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Just 40 minutes southwest of Des Moines, Winterset is a charming small town in Madison County, full of history, scenic drives, and family-friendly things to do.
It’s best known for its famous covered bridges (Yes, the Bridges of Madison County!), being the birthplace of actor John Wayne, and its beautiful rolling countryside.
If you’re planning a visit, here are the best things to do in Winterset, Iowa—with kids or without!
👉 Hi! I’m Katie, and I help busy moms plan doable, realistic, and worth-it family vacations—without losing their minds. Winterset has become one of our family’s favorite easy day trips from Des Moines, and I’m excited to share what makes it so special.
Winterset City Park
Our first stop in Winterset is always Winterset City Park, a beautiful park filled with winding woods and towering mature trees.
It’s more than just open green space—this is one of my favorite places to visit in the fall, when the trees turn brilliant shades of red, yellow, and orange. 🍁
The setting itself makes this park worth the stop, and there’s so much to do here for families.
Clark Tower
This castle-like limestone tower offers sweeping views of the countryside.
You can hike up from the parking lot near the park entrance, or drive the one-mile gravel road through the woods (which is what we usually do with kids).
Inside the tower, a winding staircase and ladder lead to the very top, where the views are incredible.
What Our Kids Love: My kids love this stop because they can climb right into the open windows on the bottom level and then tackle the steep ladder stairs all the way to the top. It feels like their own little castle adventure! 🏰
Playgrounds
Winterset City Park has two fantastic playgrounds that are always a hit with our kids.
The largest playground is especially unique—it includes a replica of Clark Tower and a covered bridge, tying in Winterset’s history in such a fun way.
It’s also an inclusive playground, designed so kids of all abilities can enjoy it.
The second playground is nearby and just as fun, making it easy to mix things up.
Both are surrounded by those tall shade trees that make the park so beautiful in every season.
What Our Kids Love: The replica play structures give them the feeling of climbing their own mini tower and bridge—so even when we’re not exploring the real ones, they still get the adventure.
Hedge Maze
Another favorite stop in Winterset City Park is the hedge maze.
My kids could spend forever in here racing through the twists and turns. It’s actually more challenging than it looks, which makes it fun for adults too!
We’ve gotten “lost” more than once—and that’s half the adventure.
What Our Kids Love: The challenge of “beating the maze” and hiding from each other in the maze (which is not too hard to do!).
Cutler-Donahoe Bridge
This historic covered bridge was built in the 1870s and relocated to City Park in 1970.
It’s one of Madison County’s six remaining covered bridges, and the easiest to visit since you can simply walk to it from the playgrounds and hedge maze.
John Wayne Birthplace Museum
Even if you’re not a huge Westerns fan, the John Wayne Birthplace Museum is a unique stop in Winterset.
It’s the only museum in the world dedicated to John Wayne, and you can tour his actual birthplace home.
Inside, you’ll find:
- A collection of costumes, posters, and film memorabilia.
- A small theater showing clips from his films.
- A gift shop with John Wayne-inspired souvenirs.
📍 Location: Just a block off Winterset’s historic town square.
Explore Downtown Winterset
The historic square in downtown Winterset is worth a stroll. Families will find:
- Madison County Courthouse – A stunning piece of architecture in the center of town.
- Shops & Boutiques – From antiques to gifts, it’s fun to browse.
- The Iowa Theater – A beautifully restored historic theater.
- Frostee’s Ice Cream Shop – An old-fashioned favorite just a block from the square. My kids vote this a must-do! 🍦
The Bakery Unlimited 🍩
Located right next to the Iowa Theater, this bakery recently received national recognition as the #3 Best Donut Shop in the U.S. (USA Today 10Best 2025 Reader’s Choice Awards). We stopped here recently, and I can absolutely confirm—it deserves the honor! The donuts were incredible, and this is now a must-do stop for us every time we’re in Winterset.
👉 Start your downtown visit at the Madison County Chamber of Commerce Welcome Center for maps and tips, especially if you plan to drive the covered bridge route.
The Covered Bridges of Madison County
No Winterset visit is complete without seeing the famous covered bridges.
Madison County has six remaining bridges, each with its own story.
- Cutler-Donahoe – Inside City Park (easy to visit).
- Cedar Bridge – 6 minutes from the square.
- Holliwell Bridge – 8 minutes from the square (and the longest).
- Hogback Bridge – 9 minutes from the square, with scenic views.
- Roseman Bridge – 17 minutes from the square, made famous by The Bridges of Madison County movie.
- Imes Bridge – The oldest, built in 1870, about 18 minutes away.
🚗 Suggested Driving Loop: Starting at the downtown square, the full loop takes about 1.5 hours. Grab a map from the Chamber of Commerce before heading out.
Monumental Park
For a quick but meaningful stop, check out Monumental Park, one of the first Civil War monuments in Iowa.
The park features a tall monument, four cannons, and cannonballs—perfect for a short history lesson with kids.
📍 Location: Just a few blocks from downtown.
Bonus Stop: Rusty Star Alpaca Farm 🦙
Just 10 minutes from Winterset City Park, this family-owned farm is such a fun and unique stop, especially with kids.
You can meet and feed the alpacas, shop the gift store for alpaca-fiber products, and learn about how they’re cared for.
It’s a quick, doable stop that adds a hands-on animal experience to your Winterset trip.
What Our Kids Love: Feeding the alpacas and watching their silly expressions—it always makes them laugh.
Mom Tip: Check the Rusty Star Alpacas Facebook page for the most up-to-date hours before you go.
Where to Eat in Winterset
- Mi Pueblito Mexican Restaurant – Great family-friendly option if you want a sit-down meal.
- Frostee’s Ice Cream – A kid (and mom) favorite for a sweet treat or a quick lunch too!
- The Bakery Unlimited – Award-winning donuts worth the stop.
Plan Your Day Trip to Winterset, Iowa
Winterset makes the perfect day trip from Des Moines for families.
Between the covered bridges, amazing city park, a donut stop, and even an alpaca farm, there’s enough to keep everyone entertained without feeling rushed.
If you’re road-tripping through Iowa, you may also enjoy:
- Top Family-Friendly Day Trips from Des Moines
- Things to Do in Pella, Iowa with Kids
- Best Things to Do in West Des Moines with Kids
- Top 10 Things to do in Iowa City with Kids
Final Thoughts on Winterset with Kids
Winterset truly shines as one of Iowa’s most charming small towns.
Whether you’re chasing history, scenic drives, famous spots, or family fun outdoors, it’s a doable and worth-it getaway that proves family trips don’t have to be complicated.
🌟 Explore More Close-to-Home Adventures
Winterset is just one of the many fun spots you can explore around Des Moines with your family.
👉 Grab my FREE Des Moines Bucket List Checklist and start checking off the best family-friendly activities in the metro—perfect for weekends, school breaks, or whenever you need a doable adventure.
May you LOVE your adventure! KW
