There are some truly unique places in the Hawkeye State; bizarre sites sure to make you stop and do a double-take. From a larger-than-life bull to a massive strawberry, some of America’s finest and most fascinating roadside attractions can be found in little old Iowa! And if you’re looking for a total treasure trove of roadside attractions, visit the small town of Winterset, Iowa.

Winterset, Iowa, is a charming town of just over 5,000 residents that's a perfect slice of Midwest living.
Ezhiki/Wikimedia Commons
Winterset doesn't only boast one of the most delightful downtowns in Iowa, it's also home to numerous roadside attractions and points of interest that are well worth checking out.
Guimir/Wikipedia
Located in Madison County, the Covered Bridge Capital of Iowa, Winterset is a delightful destination for covered bridge enthusiasts.
Roseman Covered Bridge, Elderberry Avenue, Winterset, IA, USA
larrybraunphotography.com/Moment Collection via Getty Images
Built in 1884 by Benton Jones over the North River, the Hogback Covered Bridge is a beautiful 106-foot bridge that was one of the original 19 covered bridges in Madison County. Only six remain, today, though we're partial to this bright red beauty.
Hogback Covered Bridge, Hogback Bridge Road, Winterset, IA, USA
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When you visit this roadside attraction, be sure to leave a note about your experience in the journal! It's fun reading about all the adventures folks have at this iconic Iowa bridge.
QueenMiller3/TripAdvisor

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Something you might not expect to see in Winterset, Iowa, is... a castle?
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A hidden gem located within the heart of Winterset City Park, the historic Clark Tower is a 25-foot-tall limestone monolith built in 1926 for the 80th anniversary of the founding of Iowa's iconic Madison County.
Winterset City Park, E. South St and, S 9th St, Winterset, IA 50273, USA
Bruce H/TripAdvisor
And no visit to Winterset would be complete without stopping at the birthplace of the town's most legendary resident, Mr. John Wayne.
B R/TripAdvisor
Located in town, you'll find the humble house where Wayne (nee Marion Robert Morrison) was born in 1907. The home is now the John Wayne Birthplace & Museum, an attraction celebrating this legendary Hollywood film star -- and his connection to the Hawkeye State.
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Photo ops abound at this only-in-Iowa museum, and we recommend posing with this Mr. Wayne monolith out front! Because of all the roadside attractions in Winterset, Iowa, this might just be our favorite.
John Wayne Birthplace & Museum/Facebook

Have you visited these roadside attractions in Winterset, Iowa, before? If so we’d love to hear about your experiences… and see your photos! What are some of your favorite things to do in Winterset Iowa? For more only-in-Iowa oddities, check out this list of our favorite roadside attractions in Hawkeye State.

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More to Explore

More to do in Winterset Iowa

Chris Muras | December 01, 2022

What are the top sites in Madison County?

Madison County, Iowa has a rich history. Plus it is well known and loved for its covered bridges and for the fact that John Wayne was born here. Winterset, Iowa is the hub of activity in the county with many attractions and historic sights to see. Some of the best attractions in Madison County include:

1. John Wayne Museum
2. The Iowa Theater
3. Hogback Bridge
4. The Iowa Quilt Museum
5. Winterset City Park
6. Cedar Bridge
7. Harmon Tunnel
8. Cutler - Donahue covered bridge
9. Winterset Cidery
10. Clark Tower
11. Pammel State Park

Are there really covered bridges in Madison County Iowa?

Thanks to the popular book and movie, everyone has heard about the bridges of Madison County, but are there actually covered bridges in Madison County? Why yes there are! Madison County, Iowa originally had 19 covered bridges but due to disrepair, expansion projects, and simply the effects of time, only six remain today. Five out of those six are listed on the National Register of Historic Places.

Where are the real bridges of Madison County?

The actual bridges of Madison County you may know and love, including the Roseman Covered Bridge, are in Winterset, Iowa. As you would imagine, Winterset is located in Madison County, IA. The largest town in Madison County is Winterset, which is located about 30 miles southwest of Des Moines.

Where is the largest covered bridge in the United States?

While the bridges in Madison County, Iowa may be the most famous, the largest covered bridge is in Ashtabula, Ohio. This bridge, which passes over the Ashtabula River, is 613 feet long. This beautiful covered bridge is a relatively recent addition to our covered bridge bucket list, having been built in 2008. The longest historic covered bridge is a 449-foot-long bridge in Vermont which was built in 1866.

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Winterset, IA 50273, USA