Get to Know: Winterset

Winterset is in the heart of Madison County, the “Covered Bridge Capital of Iowa” (yes, this is “The Bridges of Madsion County” from the book and movie). The quite enclave is located in the western portion of the Greater Des Moines (DSM) region and offers plenty of charm in an idyllic setting.  

When you live in Winterset, the Madison County Covered Bridge Festival happens in your backyard, every October. It includes tours, horse-drawn wagon rides, blacksmith demonstrations, a parade, live music and even a nighttime Civil War cannon firing. Also in Madison County are the John Wayne’s Birthplace & Museum, Iowa Quilt Museum, Winterset Cidery and several wineries. Four miles southwest of Winterset is Pammel State Park, a space that provides a recreational area featuring cabin rentals, canoeing and kayaking, geocaching, trails and more. Enter the park through the Harmon Tunnel, Iowa’s only highway tunnel.  

Alongside these highlights, you’ll find a community with small town appeal, with an easy commute and ready access to other areas of DSM. 

Madison County bridge

Winterset at a Glance

  • Population: 5,309 (2021, US Census Bureau) 
  • Location within Greater Des Moines: Southwest 
  • Type of Community: Mid-Sized Town 
  • School District: Winterset Community School District  
  • County: Madison 

Winterset in one sentence: Winterset is home of the Bridges of Madison County and birthplace of John Wayne, The Duke himself.  

The top five best things about Winterset: It’s small, it’s a close-knit community, there is a passion for small businesses and owners, it’s beautiful and ‘Iowa Nice’ is the real deal. 

Hidden Gems and Unexpected Finds in Winterset: See the lavender blooms located on 20 acres at PepperHarrow Farm or see a John Wayne classic at the John Wayne Matinee Series at Winterset’s historic Iowa Theater. Madison County has a growing agritourism industry and the county is proud to have many farms that offer the opportunity to connect with the beautiful scenery of Madison County and livestock.   

Community Traditions and Annual Events: The annual Covered Bridges Festival takes place the second full weekend of October. The Friday after Thanksgiving, you can catch the annual Festival of Lights in Winterset’s courthouse district. During the second weekend of December, head to the Winter Solstice Market. Finally, don’t miss the John Wayne Birthday Celebration in May! 

Best Ways to Get Connected: Winterset Newcomers meets the third Thursday of the month. Community clubs such as the Lions, Kiwanis, Rotary, Optimist or the Madison County Women’s Giving Circle are ways to get connected and serve the community.

Big Things on the Horizon for Winterset: Winterset’s Madison County Conservation Center is now open, with programming and year-round events being added for people of all ages, including self-guided identification and scavenger hunts and more. Winterset was added as a Cultural District by the Iowa Department of Cultural Affairs.  

If you’re coming to check out the community, be sure to spend your day ... : visiting the six historic Covered Bridges, exploring one (or more!) of Madison County’s amazing museums: the Madison County Historical Complex, John Wayne Birthplace & Museum, the Iowa Quilt Museum. Shop and support local at 73 local merchants around the Historic Winterset Courthouse District. Be sure to visit wineries, breweries and cideries such as Covered Bridges Winery, Winterset Cidery, Big Rack Brew Haus and 1st Down Brewing.  

Some of the ways Winterset and Madison County advances diversity, equity and inclusion (DEI): The Madison County Chamber of Commerce has been increasingly focused on advancing DEI by presenting works by and about women, women’s history and the LGBTQ+ community. An example of this would be the recent exhibit of quilts that celebrated women’s right to vote displayed at the Iowa Quilt Museum. A memorial park was created to celebrate the life and work of George Washington Carver who was a Winterset resident from 1888-1890. Local historians have been hard at work documenting and interpreting the County’s involvement in the Underground Railroad. Performance venue and public spaces within the district are ADA-accessible and updates continue to be made to these sites and spaces to increase accessibility. Winterset is a rural community with a lot of socioeconomic diversity; therefore, our artistic and cultural organizations and venues strive to provide scholarships for classes and workshops, low admission fees to performances, events, festivals and showings of family-friendly films, to name a few. As one resident articulated, “I love that Winterset is rural in its roots and honors that, but also has a modern cultural vibe with the plethora of artists and crafts persons.” DEI strategies include bringing together and cultivating more diverse programs and artists through the creation of an artist-in-residence program (particularly LGBTQ+, female, disabled, and/or artists of color). Winterset is working to depict its cultural history through public art, including painted murals, and celebrate lesser-known Winterset artists or cultural figures, including John Rox and author Charles Trumbull White.