Things to Do in Winterset, Iowa: Covered Bridges & More

Winterset is the kind of town Hollywood spent a whole movie falling in love with and then, being Hollywood, mostly forgot to visit. Meryl Streep and Clint Eastwood got a four-day romance out of these covered bridges; you can get the whole county in a weekend and still be home before the ice cream melts in the cooler. So you've typed "things to do in winterset iowa" into your phone, half-expecting three results and a grain elevator. Good news: this little Madison County seat, a comfortable drive southwest of Des Moines, is stacked with the kind of stuff that photographs better than it has any right to.

Here's the short version before we get into it. Winterset is a covered-bridge town, a John Wayne town, and a proper old-fashioned courthouse-square town, all inside a few square miles of rolling farmland. You can do it as a day trip. You'll wish you'd stayed longer.

Still reading? Then you're the type who wants the real itinerary, not the postcard. Let's walk the county.

The covered bridges of Madison County

This is the headliner, and it earns it. Madison County still has a handful of historic covered bridges scattered down its gravel roads, and yes, these are the bridges, the ones the book and the movie made famous. They were roofed for a very practical reason, not a romantic one: covering the wood decking made the timbers last decades longer. Iowa farmers weren't being sentimental. They were being cheap, which around here is a compliment.

The ones people actually drive out to see:

• Roseman Bridge — the star of the story, and the most photographed of the bunch. Red, weathered, sitting over a quiet creek like it's waiting for its close-up.
• Holliwell Bridge — the longest still standing, and an easy favorite for that low-sun, end-of-day light.
• Cedar Bridge — the one closest to town, and the one that's been rebuilt after fire more than once. Local stubbornness at work.
• Hogback Bridge — tucked into the north end of the county with a real middle-of-nowhere calm to it.
• Imes Bridge — the oldest of the surviving bridges, moved and preserved so it'd stick around.

A word of hard-won advice: these are on rural roads, some of them gravel, and cell signal has its own opinions out there. Download your map before you leave pavement, and give yourself more time than the drive suggests, because you will pull over more than you planned. The Roseman and Cedar sites have some visitor amenities; the others are simpler, so pack water and expectations accordingly.

Come for the movie, stay for the fact that it's dead quiet, smells like cut hay, and nobody's rushing you. That's not in the guidebook, but it's the actual reason people come back.

The John Wayne Birthplace & Museum

Here's the fact that stops people at parties: John Wayne, the Duke, the squintiest cowboy in film history, was born in Winterset, Iowa. Not Texas. Not Monument Valley. A small white house on a Winterset side street. The little birthplace home has been preserved, and next to it sits a full museum with the largest collection of Wayne memorabilia anywhere, movie posters, costumes, the works.

You do not have to be a die-hard Western fan to enjoy this. You mostly have to enjoy the sheer improbability of it, that one of the biggest movie stars of the twentieth century got his start in a town this size. Hours and admission shift with the season, so check the current details before you drive out. It's an easy pairing with a walk around the square.

The town square and courthouse

Winterset's square is what a lot of towns wish theirs still looked like: a limestone county courthouse anchoring the middle, and a ring of brick storefronts around it that never got bulldozed for a parking lot. This is where you slow down. Grab a coffee, poke through the shops, find a bakery, sit on a bench and watch a town that isn't in a hurry.

A loose plan for an afternoon on and around the square:

1. Coffee and a pastry to start, because you've earned it after the gravel roads.
2. A lap of the local shops and whatever's in the storefronts that week.
3. Lunch somewhere on the square, then the museum a few blocks over.
4. Ice cream or a treat before you point the car back toward wherever you're staying.

None of this needs a reservation or a plan B. That's the charm. If you've spent a weekend in a bigger place lately, this is the pace correction you didn't know you needed.

Clark Tower and the city park

Up in Winterset City Park, tucked into the trees, there's a squat limestone tower that looks like it wandered off the set of a much older, much more European movie. That's Clark Tower, a memorial built decades ago, and the payoff is the view: climb up and you get the Middle River valley laid out below you, all rolling green and river bend. The road up is narrow and a little adventurous, so take it slow, but it's worth the wiggle.

The park itself is a fine, low-key stop, trails, shade, room for the kids to burn off the car ride, a good place to eat a sandwich you brought instead of buying. If your crew has more energy than your itinerary, this is where you spend it.

The Covered Bridge Festival (and the best time to come)

Once a year, usually in October, Winterset throws the Covered Bridge Festival, and the sleepy square turns into a proper crowd, craft vendors, food, music, and the fall colors doing their thing over the bridges. It's the county's biggest weekend by a mile. Exact dates move year to year, so look up the current schedule before you build a trip around it.

Two honest notes about timing:

• Festival weekend is peak Winterset, gorgeous and lively, but also the busiest, so lodging in the area books up early. If this is your plan, plan ahead.
• Any other week in fall gives you the same colors, the same bridges, and a fraction of the crowd. For a lot of travelers, that trade is worth it.

Making a weekend of it

Winterset is genuinely doable as a day trip from the metro, but it's a shame to treat it that way. Base yourself in the area, and you can do bridges and the museum one day, the square and the tower the next, and still have time to poke around the wider region, which is exactly what a well-placed home lets you do without living out of the car.

If you're building a bigger Central Iowa trip around it, Winterset pairs naturally with a day in the capital, so it's worth skimming our guide to the best things to do in Des Moines, and if you're a Cyclone household, our weekend in Ames guide covers the other direction. A car and a couple of days, and you've got a whole corner of Iowa handled.

That's the thing about a covered-bridge weekend: it works best when the lodging just quietly does its job while you're out chasing gravel roads and golden hour. That's the whole idea behind what we do, a comfortable, well-placed home you don't have to think about, so all your attention goes to the trip.

The bottom line on things to do in Winterset, Iowa

Bridges, the Duke, a courthouse square that time was kind to, a stone tower with a view, and one big October weekend a town builds itself around. Winterset is small, and that's exactly the point, it's a full, unhurried weekend hiding an hour off the interstate. Come see why a movie fell for it.

Ready to actually go? Book a Stay-A-While home in the Des Moines area and use it as your base camp for the covered bridges, the square, and the whole Madison County ramble.