The Best Things to do in Winterset, Iowa

Winterset, Iowa is a perfect snapshot of small town America. While most people come to visit the famed covered bridges, you will be surprised how much there is to do! Here is a list of our favorite things to do in Winterset, Iowa.

If you stay overnight, I would recommend the Cobblestone Inn & Suites. This is a new hotel that is very clean and offers a free hot breakfast.

1. the Bridges of Madison County

Made famous by the 1995 movie with Meryl Streep and Clint Eastwood, the bridges still draw many people to this area. There are six remaining bridges although only one of them can actually be driven over. For more information about the covered bridges, click here.

2. John Wayne Birthplace & Museum

The museum contains many belongings of Hollywood legend John Wayne as well as memorabilia from his movies. The museum stands beside his modest childhood home which you can also tour. With only four small rooms, it won’t take too much time to walk through. It was interesting listening to the docent tell stories about John Wayne’s life.

3. Have a treat at The Bakery

Located right in the center of town, The Bakery serves up the best apple fritters and doughnuts you will ever taste! My favorite was the glazed doughnuts.

4. Winterset City Park

This lovely 76 acre park is a beautiful place to spend time on a nice day. Make your way through the hedge maze, walk across the Cutler-Donahoe Covered Bridge and see the stone bridge where Meryl Streep and Clint Eastwood had their picnic in the Bridges of Madison County.

Climbing the castle-like Clark Tower will have you feeling like Rapunzel. Note that it is a mile long drive up into the woods but the road is windy and narrow. You could walk but it will take about an hour. The road is just past the Cutler-Donahoe Covered Bridge and there will be signs directing you where to go.

5. Take pictures with murals

Across from the town square, there is an alleyway off of John Wayne Drive with several interactive murals. My son and I had so much fun taking pictures there. He fought off a dragon and played Nintendo with Mario.

6. Eat at Montross Pharmacy

At the back of Montross Pharmacy is “The Fountain” where most of the locals hang out. My son got a kick out of sitting on the stools at the bar that were like an old diner. They recommend the burger basket.

7. The Madison county historical complex

The Madison County Historical Complex has various structures and exhibits you can visit to view civil war items, quilts, early farm machinery and Native American artifacts.

Their mission is the engage the public in the heritage, culture and preservation of Madison County history.

8. Iowa Quilt Museum

The Iowa Quilt Museum is a quick stop, but worth a visit. Their mission is to promote appreciation of the American quilt and the art of quilting through displays of quilts and information about quilt history.

9. Shop at the Ben Franklin

The Ben Franklin is a large variety store that has a little bit of everything. The store has been in business since 1939. It’s a fun stop for kids to find an inexpensive toy. Harry picked out gumby and hasn’t stopped playing with it since.