Best Things to do in Winterset, Iowa

Winterset, located about 40 minutes from Des Moines in Madison County, Iowa, is such a quaint town with so much history and even quite a bit of notoriety. 

For one, the renowned Bridges of Madison County was filmed in Winterset. Additionally, Winterset is the birthplace of actor John Wayne. 

This picturesque town is also known for all of its covered bridges. 

The drive to Winterset on its Covered Bridges Scenic Byway is absolutely stunning with its rolling hills and scenic views. 

Once you make the drive to Winterset, you might be wondering what exactly to do and where to start your journey here.

Keep reading to find out all the best things to do in Winterset, Iowa. 

Winterset City Park

When we drive to Winterset with the kids, our first stop is usually Winterset City Park. We LOVE this park for so many reasons.

For one, there is SO much to do here. Secondly, it is such a gorgeous park. There are so many humongous trees that just add to the beauty of it!

Clark Tower

Our first stop in Winterset City Park is usually Clark Tower.

To get to Clark Tower, you can park in the parking lot right when you enter the park and hike to the tower or alternatively, you can drive up there.

We always drive up to the tower so I have never hiked it. The drive is about a mile to the tower and is mostly on a gravel road that winds through the woods. 

I would suggest driving to it but if you are in for a hiking adventure, go for it!

Clark Tower reminds you of a castle. The limestone tower has three stories. First is the bottom level that you can walk right into and see out the open windows, then there is a winding staircase to another level with windows, and finally you have to climb a ladder to get to the very top of the tower. 

The views at the top are AMAZING!

On its sign, it says that Clark Tower was built in 1846 in memory of Caleb and Ruth Clark who were the pioneer settlers of Madison County.


After Clark Tower, we do the one mile drive out to the main area of Winterset City Park, and then head to the playground. 

Recently, a new playground was built in this park so now there are two places for the kids to play. On our visit, we made sure to check out both of them. 

The older playground is right next to the bathrooms which is a plus!

Thankfully, Winterset City Park has so many mature trees so the park actually has some great shade in the summer months.

In the fall, the kids LOVE running through the grassy area at the park that is usually filled with leaves. 

Hedge Maze

Another super unique thing to do in Winterset City Park is the hedge maze.

The kids always have a blast with it!

The maze is actually quite challenging. It usually takes us a bit to get through it which makes it that much more fun!

Cutler-Donahoe Bridge

After completing the maze, we usually walk over to the Cutler-Donahoe covered bridge. 

This bridge was built around 1870. 

Fun Fact: This bridge was once located across the North River before it was moved to Winterset City Park in 1970.

Winterset City Park also has an historic log cabin, a few wooden sculptures to see, and a campground. 

The great thing about the park is that besides the short drive up to Clark Tower, you can simply park in a parking spot and easily walk to all of these activities and sights. They are all easily seen from the center of the park.

Winterset City Park is definitely an exciting place to see and spend time on your visit to Winterset. 

John Wayne Birthplace Museum

The John Wayne Birthplace Museum is another unique thing to check out while in Winterset.

This museum is open seven days a week except for some major holidays. 

Visitors can view all the artifacts in the museum as well as tour John Wayne’s birthplace house. 

Besides its extensive collection of John Wayne artifacts, the museum also has a theater and gift shop. 

Tickets must be purchased at the museum. 

The museum is just about a block from downtown Winterset.

Statue of John Wayne with the John Wayne Birthplace Museum building in the background

Downtown Winterset

No visit to Winterset is complete without at least a drive through its historic downtown. 

I would actually recommend parking and spending some time walking around downtown if you have the time.

If you have never been to Winterset before, I would suggest starting your day by stopping at the Madison County Chamber of Commerce Welcome Center.

This is a great place to get some information and some maps which are super helpful if you want to drive to visit some of the covered bridges in the area.

Also, downtown has some great shops and restaurants to check out!

The historic Iowa Theater is also downtown as well as the gorgeous Madison County Courthouse.

Just a block from the town square is also the delicious and historic Frostee’s ice cream. This is definitely a must have treat on your visit to Winterset.

Covered Bridges

Another must see attraction on your things to do in Winterset list should be the covered bridges. 

Madison County has six covered bridges to visit. 

If you want to see one of the covered bridges but not wanting to spend a bunch of time driving around, you can make sure to see the Cutler-Donahoe Bridge in the City Park. 

Listed below is the approximate driving time from the Winterset Town Square to each of the covered bridges.

  • Cutler-Donahoe Covered Bridge – 3 minutes
  • Hogback Covered Bridge – 9 minutes
  • Cedar Covered Bridge – 6 minutes
  • Holliwell Covered Bridge – 8 minutes
  • Roseman Covered Bridge – 17 minutes
  • Imes Covered Bridge – 18 minutes

Each of the bridges are all in different directions surrounding Winterset.  

The quickest driving route between each of the bridges starting and ending at the Winterset Chamber of Commerce located in the town square that I was able to find using Google Maps is 1 hour and 34 minutes.

The route includes starting at the Winterset Town Square and proceeding to Roseman Covered Bridge, Hogback, Cedar, Cutler-Donahoe, Holliwell, and Imes, and back to the downtown. 

To download a map of the Bridges of Madison County, click here.

Monumental Park

Another quick and free thing to do in Winterset is visit Monumental Park. 

This is a beautiful small park located near downtown.

Monumental Park was one of the first Civil War monuments constructed in Iowa. 

Besides the main monument, there are also four cannons to view plus some cannonballs. 

It is an extremely well-kept park. I highly suggest stopping by here on your visit to Winterset. 

Winterset is such a special town with so much beauty to see and things to do. I hope this list of things to do in Winterset helps you plan your road trip to this amazing little town.

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Discover some more amazing day trips from Des Moines here. May you LOVE your adventure! KW

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