If you’re looking for a small-town getaway with big charm, I think Winterset, Iowa might just steal your heart. I stumbled across it on a road trip through the state and was immediately drawn in by its peaceful vibe and storybook setting. Visiting the John Wayne Birthplace Museum in the historic town square felt like stepping into a piece of American history. You’ll love exploring the rolling hills and scenic countryside—it’s the kind of place that invites you to slow down and stay awhile.
When I Think You Should Go
I usually recommend visiting Winterset in the spring through fall (April–October). You’ll catch blooming flowers in spring, vibrant foliage in autumn, and local favorites like the Covered Bridge Festival. I’ve also been during the winter, and while it’s quieter, there’s something magical about the holiday lights and that small-town coziness.
How I’d Get to Winterset
- By Car: I typically drive in from Des Moines—it’s an easy 35-mile trip along U.S. Route 169 and Iowa Highway 92. You’ll enjoy the drive through the Iowa countryside.
- By Plane: When I fly, I use Des Moines International Airport (DSM). From there, it’s about a 45-minute drive. I always recommend renting a car so you can explore the area at your own pace.
- By Bus: If you’re taking a bus to Des Moines, you’ll need a rental or rideshare to get to Winterset. I’ve done it that way before, and it’s pretty straightforward.
Where I’ve Stayed—or Think You’d Enjoy
- Covered Bridge Inn – I stayed here on my first visit. It’s comfortable, the service is friendly, and you’ll be close to downtown and the bridges.
- Heavenly Habitat Bed & Breakfast – This one’s special. It’s in a former church, and I loved the cozy rooms and the homemade breakfast. You’ll feel like you’ve found a hidden gem.
- Hotel Greenfield (Nearby) – If you don’t mind being about 30 minutes out, this boutique hotel makes a great romantic base. I’ve recommended it to couples who want something quiet and historic.
Things to Do in Winterset, Iowa
John Wayne Birthplace & Museum - Explore memorabilia and discover sights from an exciting Western legend.
Iowa Quilt Museum - Admire intricate quilts and enjoy an unusual artistic stop.
Cedar Covered Bridge - Walk along this romantic, historic bridge featured in a beloved story.
Covered Bridges Winery - Savor local wines and relax during a peaceful weekend trip.
Iowa Theatre - Catch a classic film and enjoy an affordable, small-town movie night.
Pammel State Park - Hike scenic trails and explore nature on a fun family outing.
In Summary...
(and if you want to revisit my photo journey)