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23 Great Things To Do In Winterset

We have all heard of the celebrated Madison County in Iowa. Though some might be scratching their heads as to recall why. Perhaps the names Clint Eastwood and Meryl Streep can help ring a bell. Or maybe even the mention of the covered bridges will spark a bulb over your head.  

Oh yes, those famous covered bridges that are scattered around Madison County have brought tourists to the area since long before the famous movie starring Eastwood and Streep came out in 1995. The town nestled in midst of Madison County is Winterset, Iowa – and there’s a lot more to do than just see its bridges.

Photo courtesy Tiffany Nation

Plan a day or weekend away to tour this town and its surrounding area for history and fun with these things to do around Winterset, Iowa.

Visit A Local Museum

Step into the local home where John Wayne, born Marion Robert Morrison, was born in 1907. While there take a tour of the John Wayne Museum, said to be the only museum in the world dedicated to John Wayne.

Exterior of John Wayne Birthplace and Museum
Photo courtesy Tiffany Nation

Or if brightly colored fabrics and patchwork quilts speak your love language, stop in at the Iowa Quilt Museum. With ever changing exhibits there is always a reason to go back to visit the beautiful artwork and cultural history of the quilts on display.

  1. John Wayne Birthplace and Museum, 205 S. John Wayne Drive
  2. Iowa Quilt Museum, 68 E. Court Ave.

Tour The Covered Bridges Of Madison County

Spanning throughout the County of Madison, there are six covered bridges still standing. Spend the day driving along the country roads and stepping foot onto these astonishing bridges. 

Hogback Bridge in Madison County, Iowa
Photo courtesy Tiffany Nation

The two most prominent bridges that were featured in the film “Bridges of Madison County” are the Holliwell Bridge and the Roseman Bridge. As the bridges are spread throughout the county, plan for at least an hour or more of drive time to see all of the bridges.

  1. Cedar Bridge, 1874 Nature Court
  2. Cutler-Donahoe Bridge, 300 S. Ninth St.
  3. Hogback Bridge, 1879 Hogback Bridge Road
  4. Holliwell Bridge, 123 Holliwell Bridge Road
  5. Imes Bridge, 500 E. Main St., St. Charles
  6. Roseman Bridge, 2451 Elderberry Ave.

Related post: Of course seeing at least one of these bridges is a top thing to do in the state!

Enjoy The Afternoon With A Drink (Or Two)

Stop in at a local winery and sip on wine named after one of the local bridges or have a glass of a bourbon barrel red. If wine isn’t your go to, you can stop at the local hard cidery. 

Madison County Winery glass and sample cards
Photo courtesy Tiffany Nation
  1. Covered Bridges Winery, 2207 170th Trail
  2. Madison County Winery, 3021 St. Charles Road, St. Charles
  3. Two Saints Winery, 15170 20th Ave., St Charles
  4. Winterset Cidery, 1638 US-169 (open seasonally)

Take In A Movie

Make a stop at The Iowa Theater located in downtown Winterset. Built in approximately 1899, this theater is still available for patrons to visit and to take in entertainment. 

  1. The Iowa Theater, 121 John Wayne Drive

Climb A Tower

Live your best Rapunzel moment and sit atop of a tower that overlooks the Winterset City Park. This 25-foot limestone castle was built in 1926 and is definitely a sight to see.

Clark Tower at Middle River Park in Winterset
Photo courtesy Tiffany Nation
  1. Clark Tower, Middle River Park, 2278 Clark Tower Road

Visit A Park

From cable suspension bridges to wetlands, to nature center activities or staying in a yurt – there are all kinds of things to experience in one of the many parks located around Winterset. Take a hike for a day or camp overnight. There is fishing, canoe access, playgrounds and more. 

For a full listing of parks and recreational activities be sure to visit the Madison County Parks and Conservation Center online.

  1. Pammel State Park, 1900 Pammel Park Road
  2. Middle River Park, 2278 Clark Tower Road
  3. George Washing Carver Park, 112 E. Court Ave.
  4. Winterset City Park, East South Street and South Ninth Street
  5. Winterset Aquatic Center, 1201 W. Jefferson St.

Stay At A Bed & Breakfast

A short 30-minute drive from Winterset is well worth it for an overnight stay at the Longview Farms Bed and Breakfast. With hot tea and treats waiting for your arrival, you will be spoiled from the start of your stay. 

Breakfast at Longview Farms Bed and Breakfast in Winterset
Photo courtesy Tiffany Nation

A cozy stopover at the farm is never complete without a large, homemade breakfast.

  1. Longview Farms Bed and Breakfast, 3220 Wyoming St., New Virginia

Attend A Festival

Tour the town and area during a festival. This spring, celebrate John Wayne’s birthday. 

During the fall, be a part of the Covered Bridges Festival which includes vendors, activities, entertainment, car show, quilt show and more!

  1. John Wayne Birthday Celebration, May 27-28, 2022
  2. Madison County Fair, July 20- 24, 2022
  3. Madison County Covered Bridges Festival, Oct. 8-9, 2022

About the guest writer

Tiffany Nation is a full-time working mother and wife. In her free time she loves creating, doing yoga, spending time with her family and enjoying all of what Iowa has to offer.

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