Take a Day Trip to Madison County, Iowa in DSM USA This Summer

When you live in Greater Des Moines (DSM), you’ll never need to look far for things to do and places to stay. In this new “DSM Day Trip” series, we’re highlighting different cities and counties around the region so you can see just what each of these different locations has to offer. In this post, check out Madison County, Iowa. From must-attend events to shopping, dining and hotels, Madison County is the perfect place to spend a day.

Summer Things to Do in Madison County, Iowa

Must-Attend Madison County Events

Earlham Freedom Festival

At City Park in Earlham, celebrate the Fourth of July all day long with a parade, food trucks, corn hole and a carnival. There will also be live music, fireworks and more. A baking competition will take place at Earlham Community Center, and you won’t want to miss Toby the Balloon Dude, either!

Learn more about the schedule of events on the Earlham Freedom Festival Facebook page.

Levitt AMP Earlham Music Series

Head to Earlham City Park for the City of Earlham’s free, Levitt AMP Earlham Music Series concerts taking place from 6 – 9 p.m. on Sundays. Upcoming shows include:

• July 14: Wesli
• July 21: Medusa
• July 28: Magnolia Boulevard
• Aug. 4: The Claudettes
• Aug. 11: Buckmiller-Schwager Band

RSVP for an event at earlhammusicseries.com/concerts.

Madison County Fair

This July 17 – 21, head to the Madison County Fairgrounds for the Madison County Fair where you’ll find free entertainment, carnival games, a livestock auction and grandstand events such as rodeos, mud runs and more. The Fair will have face painting, a balloon artist and more so all ages can enjoy the festivities. Attendees can even stay close to the action by camping at the Fairgrounds, too.

Learn more about the Madison County Fair at madisoncountyfair.net.

St. Charles Old Settlers

Celebrate the founding of St. Charles at the annual St. Charles Old Settlers event taking place July 19 – 21 at various locations around town. On Friday, attend the Opening Ceremony at 7 p.m. to see the King & Queen Coronation and visit food trucks until 8 p.m. On Saturday, have breakfast at St. Charles Parish Hall until 10:30 a.m., attend the 5K and Fun Run at Imes Bridge at 8 a.m. or take park in a Cribbage Tournament. Later in the day, check in for the Pedal Tractor Pull, take part in a Bags Tournament or ride the Neighborhood Trolley. The Welcome to the Neighborhood Parade begins at 6 p.m., too!

More information about the Old Settlers Reunion can be found at scoldsettlers.org.

Movies in the Park

Winterset Parks and Recreation’s Movies in the Park series at City Park has two more showings this summer. See The Super Mario Bros. Movie on Friday, July 19 and The Sandlot on Friday, Aug. 16. The movies begin at dusk, so don’t miss out on the fun!

More information can be found on the Winterset Parks and Recreation Facebook page.

Hinterland Music Festival

In 2024, Hinterland Music Festival is welcoming an awesome lineup of musicians to St. Charles Aug. 2 – 4, including headliners like Hozier (Friday), Vampire Weekend (Saturday) and Noah Kahan (Sunday). Other acts include Lizzy McAlpine, Orville Peck, Ethel Cain and Chappell Roan. One-day GA Festival Tickets are still available for Saturday night at $145 and One-Day SAINTS Tickets are still available for Friday and Saturday for $750. Car camping campsites for camping are also available.

To find out more about this year’s Hinterland Music Festival, visit hinterlandiowa.com.

Yoga at the Bridge

In Winterset City Park, attend three more dates for Yoga at the Bridge — Donahue Covered Bridge to be exact — this summer. Bring your own mat / towel / water bottle and get ready to break a sweat at 9 a.m. during this free yoga series. The final dates include:

• Aug. 3 with Selena (NADI)
• Aug. 17 with Heidi (Fit & Fierce)
• Aug. 31 with Heidi (Fit & Fierce)

Learn more about Yoga at the Bridge on the Winterset Parks and Recreation Facebook page.

And don’t miss the Paint Madison County (A Plein Air Festival) taking place Sunday, Sept. 22 this fall. It’s a time to celebrate art, creativity and Madison County all in one place! Read more about the event from Madison County Chamber of Commerce CEO Amara Huffine here.

Shopping Districts and Restaurants in Madison County

The Madison County Farmers’ Market is a small market featuring homegrown and homemade products like eggs, honey and flower bouquets, not to mention the soaps, lotions, jams / jellies and metal artwork you’ll find as you go from booth to booth in Winterset’s town square. Visit Saturday mornings from 8 a.m. until Noon now through October.

Learn about vendor products and more on the Madison County Farmers' Market Facebook page.

Madison County’s local boutiques offer opportunities for shopping local when you’re not attending an event or visiting one of the six bridges — Cedar, Cutler-Donahoe, Hogback, Holliwell, Imes and the Roseman. When it comes to custom jewelry, designs by Brooke Sutphin offer wearable options unique to b.shannon designs in Winterset. Evergreen & Lily Floral Studio is Winterset’s favorite fresh flower retailer, with designs for any occasion, including weddings. At Madison County Mercantile, shop home décor and antiques in historic downtown Winterset.

Don’t forget to dine in Madison County restaurants while you’re in the area. Talk Shop Lounge in St. Charles, Beans & Beignets in Earlham — attend NOLA Nights, a monthly New Orleans style buffet here! — and Winterset’s Easton’s Bistro or Urban on the Square are great options.

Tip: Attend the Covered Bridge Festival Oct. 12 – 13 this fall to tour all six covered bridges, see live entertainment, attend a car show and visit vendor booths.

Hotels in Madison County

Hotels in Winterset are close to nearby attractions like the John Wayne Birthplace Museum, Iowa Quilt Museum, Covered Bridges Scenic Byway and more. Stay at Hotel Greenfield, a restored and redeveloped hotel built in 1919. The refurbished hotel offers 20 room options, including two luxury suites, one with a large sitting area and the other with a private porch. Or, book a room at the Cobblestone Inn & Suites – Winterset, the Covered Bridge Inn or the Heavenly Habitat Bed and Breakfast, all in Winterset, or find a place to stay in nearby Adair or Dallas Counties.

For more information on places to stay and things to do in Madison County, Iowa, visit madisoncounty.org.

Spending a day in Greater Des Moines (DSM) means you’ll have the chance to experience local outdoor recreation areas, shopping destinations and arts and cultural activities. It’s easy to have fun with the family, make friends and take in all that the region has to offer. Find events and things to do in DSM communities all year round at DSMpartnership.com.