Winterset – Why This Is Iowa’s Best Small Town

Thirty miles southwest of Des Moines is where you’ll find a place that is quite possibly the best small town in Iowa. It’s also one of the best representations of the phrase “small town USA”. Winterset was good enough for American icon John Wayne (though he was only born here) and it’s good enough for more than 5,000 Iowans that call this town home.

My first experience visiting Winterset was in the Summer of 2014. I was filming a story on the John Wayne Birthplace, a small white house within walking distance of the town’s downtown square. Though I was only in the area for a couple of hours, I made a mental note to visit Winterset as soon as an opportunity came along.

Thankfully, it only took a year for the path to Winterset to find its way into my GPS.  This time I’d be able to explore and meet the folks that make this town tick.

best towns in Iowa
Ben Franklin is one of the stores that line the Winterset downtown square surrounding the old municipal courthouse.

Brian Downes is the Executive Director of The John Wayne Birthplace Museum. Mr. Downes, a former Chicago native, told me his initial feelings the first time he rolled into Winterset. “It didn’t even seem real. Downtown was almost like a movie set.”

In fact, some parts of the area have actually been movie sets. The classic Bridges Of Madison County film continues to make this area a hot spot for tourists passing through. On a tour of our own we crossed paths with a family from Brazil that stopped by one of the iconic covered bridges during a vacation in the states.

best towns in Iowa Winterset

Most tourists stop through to see the covered bridges or where Marion Morrison was born. (That was John Wayne’s real name.) But, a deeper dive into this small community reveals that Winterset is a special place because of the people that live here.

In what was certainly a first during my travels, I was invited to a backyard BBQ to celebrate my visit to Winterset. Kayla Hawkins, the former Tourism Director for Madison County, hosted a small gathering in the couple’s backyard. It made me wish every big city and small town showed this much hospitality and kindness.

Sitting around the table, I shared stories and laughs with locals. Locals that quickly seemed like life long friends.

Winterset IA

Corn Is Beautiful

Madison County is full of corn fields as you might imagine but it’s actually quite gorgeous as you drive along these country roads where you might not see homes or even another car for miles.  There’s also something unique about the sky in this part of Iowa – perhaps the fact that it’s so flat – you can see straight ahead for what seems like forever.

Driving around the area you’ll see barns, farms and tractors.  You might even stumble across a one room school house that’s part of the national registry of historic places. The North River Stone Schoolhouse was built in 1874 and is one of many one room school buildings spread out across the state.  Inside you’ll see the old wood burning stove that kept kids warm during the brutal Iowa winters and a list of test questions that students would be required to answer that attended class. (Hint: You’re going to fail miserably.)

best small town in iowa
Renovated one room school house that was in use until 1945. About a dozen desks are inside the limestone building surrounded by corn fields in rural Madison County, Iowa

Back downtown, it’s the John Wayne Birthplace Museum that’s bringing tourists from around the world to Winterset. The open page of the lobby’s guest book shows visitors today from Wisconsin, Oklahoma and as far away as Denmark. Inside the museum you’ll find a number of fun artifacts that tell the story of Winterset’s most well known native – including one of his cars, wardrobe pieces from films and hold your breath ladies – a display case featuring his toupee.  (Who knew?)

A short film inside the museum’s replica theater is spectacular – even for folks that aren’t familiar with the John Wayne movies.  Trivia tidbit – the seats inside are actually from the famous Chinese Theater in Hollywood.   Before you leave – you’ll have your choice of just about anything you can think of with John Wayne’s name or likeness on it in the museum’s gift shop.

The birthplace of John Wayne is right around the corner and tours are available through out the week.


Like many small towns across America – there is such character (and actual characters) that make places like Winterset so desirable. Seeing homes proudly displaying American flags, strangers that make eye contact and say hello and of course – small businesses that will remember your first name the next time you walk in the door. Those things help make a place like Winterset a strong contender for the best small town in Iowa.

Mr. Downes was right – this place doesn’t seem real.

Winterset

If you’d like more information about Madison County you can visit: http://www.madisoncoia.us/

Things To See

Here’s Where To Find The Best Murals in Kansas

best murals in kansas

Here’s An Easy Way To Tour The White House

It's the most famous building in the United States...

Best 16 Free Things To Do In St. Louis

St. Louis is hands-down one of the best places...

First Visit To Washington DC: An Ultimate How-To-Guide

Like a lot of people, I wasn't sure about...

Road Trips

27 Unique & Quirky Things To Do In Kansas

I'm always up for finding experiences that aren't the...

First Visit To Washington DC: An Ultimate How-To-Guide

Like a lot of people, I wasn't sure about...

First Trip To Oregon? Six Amazing Places You Must See!

If you're wondering how to perfectly plan your first...

8 Unique Experiences You Need To Try In Oconee County

Oconee County is a beautiful place in South Carolina...

25 Awesome Things To Do in Missouri

If you're looking for things to do in Missouri,...