If You Only Have One Day To Visit This Small Town in Iowa, Here’s Everything You Absolutely Can’t Miss

Let’s say you happen to be traveling through Iowa and are in a time crunch. You only have one day to stop along your route, and it happens to be in delightful Winterset, Iowa, a charming small town jam-packed with iconic sights, small-town warmth, and quite a few things to do. So, where do you even start? I’ve curated a day-trip adventure in Iowa that will let you see all the best Winterset offers, even when you only have less than 24 hours to explore. Let's get started.

1. Historic Downtown Winterset

Start your day in Winterset with a hot coffee and a hearty breakfast at Petite Cafe. This craft coffee and small-batch bakery offers a delicious selection for homemade treats to kick off your day the right way. Try The BAE, a bacon, avocado, and egg sandwich, with melted cheddar and spicy mayo on a freshly baked croissant, you won’t regret it. Then stroll through the historic downtown area along Court Avenue. Pop into the Iowa Quilt Museum to see some of the amazing handiwork on display there.

2. John Wayne Birth Home

John Wayne was born Marion Morrison at a humble Winterset home in 1907. You'll find it on the corner of South Second Street and East South Street. His small birthplace home is preserved as it was during his early years. After you've had a look at his birth home, head around the corner to the museum dedicated to John Wayne.

3. John Wayne Birthplace Museum

Next up, we have the John Wayne Birthplace Museum, dedicated to Winterset’s most famous native. This museum offers a look into his life and legendary Hollywood career. You can tour and explore exhibits showcasing memorabilia from his films and personal life.

The museum houses one of the largest collections of John Wayne artifacts in the world, including iconic costumes and rare photographs. This is a must-visit for fans of classic cinema, offering a fascinating glimpse into how this small-town boy grew into one of the most enduring figures in American film.

4. City Park and Historic Clark Tower

After you've paid homage to John Wayne's legacy, head to the southeast side of town and City Park. Make your way up the winding road to historic Clark Tower—Winterset's "castle"—for commanding views of the lovely Middle River valley.

5. The Bridges of Madison County

Next, let’s head over to see some of the iconic covered bridges that inspired the iconic book, The Bridges of Madison County. No trip to Winterset would be complete without visiting the covered bridges that inspired Robert James Waller’s famous novel and the subsequent film adaptation starring Clint Eastwood and Meryl Streep. There are six covered bridges scattered around Madison County, and Winterset is the perfect base to explore them.

The Hogback Covered Bridge and Roseman Covered Bridge are two of the most popular and photogenic, both located within a short drive of town. Each bridge has its unique design and history, and they’re beautiful to visit year-round, whether framed by spring greenery, autumn leaves, or winter snow.

6. Covered Bridges Winery

End the day with a stop at Covered Bridges Winery. Tucked away in the rolling hills near Winterset, this family-owned winery crafts wines from locally grown grapes, and it’s a great spot to unwind with a tasting flight. Sip on wines named in homage to the area’s covered bridges, like the white Bridges blend or the red Roseman. The tasting room offers a laid-back, welcoming atmosphere with beautiful countryside views.

For dinner, make your way to The Drift Taproom and Restaurant on the town square, a restaurant that combines Iowa comfort food with a touch of modern flair. Known for its burgers, steaks, and other classic dishes, The Drift offers a warm, cozy ambiance perfect for a satisfying evening meal. We heard the flatbreads are out of this world.

Are you dreaming about your next Hawkeye State adventure? Check out Only In Your State’s AI-powered itinerary planner to inspire your trip.