Winterset, Iowa: Best Things to Do – Top Picks

Did you know Winterset, Iowa, is home to six historic covered bridges within a 12-mile radius, earning it the nickname “Covered Bridge Capital of Iowa”? These architectural treasures, made famous by the novel and film “The Bridges of Madison County,” draw thousands of visitors each year to this charming Midwestern town of just over 5,300 residents. Beyond its bridges, Winterset offers a delightful blend of history, culture, and small-town hospitality that makes it a hidden gem in America’s heartland.

Getting to Winterset, Iowa

Winterset is located in Madison County, approximately 30 miles southwest of Des Moines, Iowa’s capital city. Most visitors arrive via Des Moines International Airport (DSM), which offers numerous daily flights from major U.S. cities. Flights to Des Moines are typically affordable and frequent, making Winterset easily accessible for weekend getaways or longer vacations.

From Des Moines, take Interstate 35 south to Exit 56, then follow Highway 92 west for about 10 miles until you reach Winterset. The drive from Des Moines takes approximately 45 minutes, offering scenic views of Iowa’s rolling countryside along the way.

Aerial view of Winterset’s historic town square with the Madison County Courthouse

Planning Your Journey to Winterset

A visit to Winterset deserves at least two full days to properly explore the covered bridges, museums, and local attractions. If you’re a photography enthusiast or nature lover, consider adding an extra day to fully appreciate the scenic countryside and capture the bridges in different lighting conditions.

For the most comprehensive experience, download the Madison County Covered Bridges Map before your visit. The Madison County Chamber of Commerce also offers guided tours for those who prefer a more structured experience with local insights.

Inside the John Wayne Birthplace Museum, showcasing memorabilia from the legendary actor’s career

When to Visit Winterset

Winterset experiences all four seasons distinctly, each offering a unique perspective on the town and its famous bridges. The best times to visit are late spring (May-June) and early fall (September-October), when temperatures are mild and the countryside is at its most picturesque.

The annual Covered Bridge Festival, held the second weekend in October, is Winterset’s signature event. The festival features arts and crafts vendors, food stalls, live entertainment, a parade, and guided tours of the bridges. While this is an incredible time to experience local culture, accommodations fill up quickly, so book well in advance if you plan to attend.

Hogback Bridge showcasing Madison County’s spectacular autumn colors

Getting Around Winterset

Having your own vehicle is essential for exploring Winterset and Madison County, especially if you want to visit all six covered bridges, which are scattered throughout the countryside. The bridges are located on rural roads, some unpaved, making a car necessary for access.

While the town itself is walkable, with most attractions in the downtown area within easy strolling distance, you’ll need transportation to reach the bridges and other rural attractions. Consider renting an SUV or vehicle with good ground clearance if you plan to visit during wet seasons, as some of the bridge access roads can become muddy.

Visitors exploring Cedar Bridge, one of Madison County’s restored covered bridges

Where to Stay in Winterset

Winterset offers a variety of accommodation options, from charming bed and breakfasts to modern hotels and unique stays. For the authentic Madison County experience, consider booking one of the historic B&Bs in or near downtown Winterset.

During the Covered Bridge Festival in October and summer weekends, accommodations in Winterset fill quickly. Consider booking at least 3-6 months in advance for these peak periods. For more lodging options, check with the Madison County Chamber of Commerce, which maintains a comprehensive list of local stays.

A charming bed and breakfast in Winterset’s historic district

Where to Eat in Winterset

Winterset’s dining scene offers a taste of authentic Midwestern cuisine with several standout local restaurants. From classic diners to farm-to-table establishments, you’ll find plenty of options to satisfy your appetite after a day of exploring.

For a quick bite or coffee break, visit Montross Pharmacy, which houses an old-fashioned soda fountain serving ice cream treats and light lunches. Mi Pueblito offers authentic Mexican cuisine, while Rodell’s Smokehouse is the place to go for barbecue enthusiasts.

The historic Northside Café, featured in “The Bridges of Madison County” film

Top Attractions in Winterset

While the covered bridges are Winterset’s claim to fame, the town offers numerous other attractions worth exploring. Here’s a guide to the must-see sights in and around Winterset:

The Covered Bridges

Madison County originally had 19 covered bridges; today, six remain and are on the National Register of Historic Places. Each bridge has its own character and story:

Museums and Historical Sites

John Wayne Birthplace & Museum

Visit the modest four-room house where John Wayne was born in 1907, then explore the 6,100 square foot museum featuring the largest collection of John Wayne memorabilia in existence. The museum showcases original movie posters, scripts, costumes, and personal correspondence from the legendary actor’s life and career.

Location: 205 S. John Wayne Drive

Website: johnwaynebirthplace.museum

The John Wayne Birthplace Museum, dedicated to Winterset’s famous son

Colorful quilt displays at the Iowa Quilt Museum on Winterset’s town square

Iowa Quilt Museum

Located on the town square, this museum celebrates the art and history of quilting with rotating exhibits featuring both historic and contemporary quilts. The museum offers regular workshops and special events for quilting enthusiasts.

Location: 68 E. Court Avenue

Website: iowaquiltmuseum.org

Outdoor Recreation

Winterset City Park

This 76-acre park features hiking trails, picnic areas, and the historic Clark Tower, a limestone observation tower offering panoramic views of the Middle River Valley. The park also contains the Cutler-Donahoe covered bridge, which was relocated here for preservation.

Don’t miss the natural limestone maze and the beautiful stone bridge built by the WPA during the Great Depression.

Clark Tower and picnic areas in Winterset City Park

For outdoor enthusiasts, the Middle River Water Trail offers kayaking and canoeing opportunities with unique views of the covered bridges from the water. Pammel Park features unique yurt accommodations, hiking trails, and Iowa’s only highway tunnel carved through limestone.

Practical Tips for Visiting Winterset

Winterset’s town square and courthouse during winter, beautifully decorated for the holidays

Annual Events in Winterset

Timing your visit to coincide with one of Winterset’s annual events can enhance your experience. Here are the major celebrations throughout the year:

The annual Covered Bridge Festival draws thousands of visitors to Winterset each October

Experience the Charm of Winterset

Winterset, Iowa, offers a perfect blend of history, natural beauty, and small-town charm that makes for a memorable getaway. Whether you’re tracing the footsteps of Francesca and Robert from “The Bridges of Madison County,” exploring the birthplace of an American film icon, or simply enjoying the peaceful countryside, Winterset welcomes visitors with open arms and authentic Midwestern hospitality.

Pack your camera and curiosity—Winterset’s bridges, history, and small-town charm are waiting to surprise you with their timeless appeal and hidden stories. As you cross through the covered bridges and stroll the historic town square, you’ll discover why this small Iowa town continues to capture the hearts of visitors from around the world.